NPASS Compound

Structure

CID46335 OpenBabel06191715382D 105119 0 0 1 0 0 0 0 0999 V2000 8.3786 0.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7029 2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8650 1.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5136 2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6757 1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3786 1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7029 3.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8650 2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5136 3.3862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6757 2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0543 0.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3786 2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1893 1.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1893 2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3786 -1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2165 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0543 -1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3786 -3.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1893 -2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1893 -3.3862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2165 0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5408 2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0272 0.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3514 1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8379 1.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2165 -1.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2165 -2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2165 2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5408 4.3537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0272 2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3514 3.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8379 3.3862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2165 -3.3862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0543 1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3786 3.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1893 2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1893 3.3862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5408 -1.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5408 -3.3862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0272 -1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0272 -2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3514 -1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3514 -2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8379 -2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8379 -2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0543 -0.9675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3786 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5408 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5408 -2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0272 -0.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0272 -1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3514 -0.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3514 -1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8379 -1.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8379 -1.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7029 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8650 -1.4512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5136 -0.4837 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6757 -0.9675 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7029 0.9675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8650 -0.4837 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5136 0.4837 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6757 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2165 -0.4837 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5408 1.4512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0272 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3514 0.9675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8379 0.4837 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3786 -1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1893 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1893 -1.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0543 -1.9350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2165 3.3862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5408 5.3211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0272 3.8699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3514 4.8374 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8379 4.3537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0543 -3.8699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8922 2.4187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2165 4.3537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3514 2.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0272 3.8699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8379 3.3862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7029 -1.9350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7029 -3.8699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8650 -2.4187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8650 -3.3862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5136 -2.4187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5136 -3.3862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6757 -2.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6757 -2.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8922 -0.4837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8650 1.4512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7029 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6757 0.9675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5136 0.4837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3786 0.9675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3786 -0.9675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1893 0.4837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1893 -0.4837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 23 1 0 0 0 0 2 7 2 0 0 0 0 2 24 1 0 0 0 0 3 8 2 0 0 0 0 3 25 1 0 0 0 0 4 9 2 0 0 0 0 4 26 1 0 0 0 0 5 10 2 0 0 0 0 5 27 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 9 33 1 0 0 0 0 10 34 1 0 0 0 0 11 23 2 0 0 0 0 11 36 1 0 0 0 0 12 24 2 0 0 0 0 12 37 1 0 0 0 0 13 25 2 0 0 0 0 13 38 1 0 0 0 0 14 26 2 0 0 0 0 14 39 1 0 0 0 0 15 27 2 0 0 0 0 15 40 1 0 0 0 0 16 28 2 0 0 0 0 16 41 1 0 0 0 0 17 28 1 0 0 0 0 17 50 2 0 0 0 0 18 29 1 0 0 0 0 18 49 1 0 0 0 0 19 35 2 0 0 0 0 19 42 1 0 0 0 0 20 43 2 0 0 0 0 20 45 1 0 0 0 0 21 44 2 0 0 0 0 21 46 1 0 0 0 0 22 47 2 0 0 0 0 22 48 1 0 0 0 0 28 76 1 0 0 0 0 29 35 1 0 0 0 0 29 72 2 0 0 0 0 30 36 2 0 0 0 0 30 77 1 0 0 0 0 31 37 2 0 0 0 0 31 78 1 0 0 0 0 32 38 2 0 0 0 0 32 79 1 0 0 0 0 33 39 2 0 0 0 0 33 80 1 0 0 0 0 34 40 2 0 0 0 0 34 81 1 0 0 0 0 35 82 1 0 0 0 0 36 83 1 0 0 0 0 37 84 1 0 0 0 0 38 85 1 0 0 0 0 39 86 1 0 0 0 0 40 87 1 0 0 0 0 41 51 2 0 0 0 0 41 88 1 0 0 0 0 42 52 2 0 0 0 0 42 89 1 0 0 0 0 43 53 1 0 0 0 0 43 90 1 0 0 0 0 44 54 1 0 0 0 0 44 91 1 0 0 0 0 45 55 2 0 0 0 0 45 92 1 0 0 0 0 46 56 2 0 0 0 0 46 93 1 0 0 0 0 47 57 1 0 0 0 0 47 94 1 0 0 0 0 48 58 2 0 0 0 0 48 95 1 0 0 0 0 49 67 1 0 0 0 0 49 96 1 6 0 0 0 50 51 1 0 0 0 0 50101 1 0 0 0 0 51 59 1 0 0 0 0 52 72 1 0 0 0 0 53 73 2 0 0 0 0 54 60 1 0 0 0 0 54 74 2 0 0 0 0 55 61 1 0 0 0 0 55 73 1 0 0 0 0 56 74 1 0 0 0 0 57 75 2 0 0 0 0 58 62 1 0 0 0 0 58 75 1 0 0 0 0 59 53 1 1 0 0 0 59 63 1 0 0 0 0 60 52 1 1 0 0 0 60 64 1 0 0 0 0 61 57 1 1 0 0 0 61 65 1 0 0 0 0 62 56 1 1 0 0 0 62 66 1 0 0 0 0 63 68 1 0 0 0 0 63 97 1 6 0 0 0 64 69 1 0 0 0 0 64 98 1 6 0 0 0 65 70 1 0 0 0 0 65 99 1 6 0 0 0 66 71 1 0 0 0 0 66100 1 6 0 0 0 67 23 1 6 0 0 0 67102 1 0 0 0 0 68 24 1 6 0 0 0 68101 1 0 0 0 0 69 25 1 6 0 0 0 69104 1 0 0 0 0 70 26 1 6 0 0 0 70103 1 0 0 0 0 71 27 1 6 0 0 0 71105 1 0 0 0 0 72102 1 0 0 0 0 73103 1 0 0 0 0 74104 1 0 0 0 0 75105 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1442.33
Volume:	1362.022
LogP:	6.046
LogD:	1.734
LogS:	-6.507
# Rotatable Bonds:	9
TPSA:	551.9
# H-Bond Aceptor:	30
# H-Bond Donor:	25
# Rings:	15
# Heavy Atoms:	30

MedChem Properties

QED Drug-Likeness Score:	0.063
Synthetic Accessibility Score:	6.935
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.747
MDCK Permeability:	4.0015976310314727e-07
Pgp-inhibitor:	0.342
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	84.23175048828125%
Volume Distribution (VD):	-0.455
Pgp-substrate:	51.95616912841797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.001
CYP3A4-substrate:	0.504

ADMET: Excretion

Clearance (CL):	9.671
Half-life (T1/2):	0.429

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.985
Carcinogencity:	0.003
Eye Corrosion:	0.003
Eye Irritation:	0.958
Respiratory Toxicity:	0.0

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC46335

Natural Product ID:	NPC46335
*Common Name:**	QRFZGLTZLZZHCM-NWYMYRDLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QRFZGLTZLZZHCM-NWYMYRDLSA-N
Standard InCHI:	InChI=1S/C75H62O30/c76-28-16-41(88)51-50(17-28)101-68(24-2-7-31(78)37(84)12-24)63(97)59(51)53-43(90)20-45(92)55-61(65(99)70(103-73(53)55)26-4-9-33(80)39(86)14-26)57-47(94)22-48(95)58-62(66(100)71(105-75(57)58)27-5-10-34(81)40(87)15-27)56-46(93)21-44(91)54-60(64(98)69(104-74(54)56)25-3-8-32(79)38(85)13-25)52-42(89)19-35(82)29-18-49(96)67(102-72(29)52)23-1-6-30(77)36(83)11-23/h1-17,19-22,49,59-71,76-100H,18H2/t49-,59-,60+,61-,62+,63-,64-,65-,66-,67-,68-,69-,70-,71-/m1/s1
SMILES:	c1cc(c(cc1[C@@H]1[C@@H](Cc2c(cc(c([C@H]3c4c(cc(c([C@H]5c6c(cc(c([C@H]7c8c(cc(c([C@H]9c%10c(cc(cc%10O[C@H](c%10ccc(c(c%10)O)O)[C@@H]9O)O)O)c8O[C@H](c8ccc(c(c8)O)O)[C@@H]7O)O)O)c6O[C@H](c6ccc(c(c6)O)O)[C@@H]5O)O)O)c4O[C@H](c4ccc(c(c4)O)O)[C@@H]3O)O)O)c2O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL592373
PubChem CID:	16129741
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)00169-2]
NPO4654	Critonia quadrangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)81431-4]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575960]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11975485]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15128023]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21446699]
NPO16601	Styrax perkinsiae	Species	Styracaceae	Eukaryota	n.a.	bark	n.a.	PMID[26762060]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31763840]
NPO12697	Baccharis megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3437280]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9748368]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16289	Marrubium supinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15760	Aconitum pseudohuiliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10247	Orthosphenia mexicana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14413	Bombus muscorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18873.8	Salmonella enterica subsp. enterica serovar typhimurium	Subspecies	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14723	Streptomyces xantholiticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15531	Quercus dentata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12438	Fomes cajanderi	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7515	Codium decorticatum	Species	Codiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10802	Rhinoceros sondaicus	Species	Rhinocerotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29175	Strychnos tabascana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14892	Flemingia congesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11233	Pseudocyphellaria impressa	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4448	Relhania pumila	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16435	Cacalia bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13872	Amanita cokeri	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14046	Stevia mercedensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24501	Asteriscus graveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9823	Centrosema pascuorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11915	Lecanora planaica	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26436	Citrus glauca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13563	Alstonia deplanchei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16856	Solanum elaeagnifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15969	Alcyonium molle	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10247	Orthosphenia mexicana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16601	Styrax perkinsiae	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9107	Metalasia bolusii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO576	Oxyanthus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4654	Critonia quadrangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12697	Baccharis megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21913	Verbesina rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14572	Senecio latifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13396	Aplophyllum popovii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16522	Ceratozamia fuscoviridis	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15760	Aconitum pseudohuiliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5468	Dacrydium fonki	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2372	Cryptotermes cynocephalus	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16766	Haplophyllum dauricum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16289	Marrubium supinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16071	Erigeron crispus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT568	Individual Protein	Matrix metalloproteinase-2	Homo sapiens	IC50	=	43200.0	nM	PMID[479865]
NPT280	Individual Protein	Matrix metalloproteinase 9	Homo sapiens	IC50	=	39200.0	nM	PMID[479865]
NPT2	Others	Unspecified		IC50	=	21400.0	nM	PMID[479865]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC46335 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	549
0.1-0.2	1799
0.2-0.3	5079
0.3-0.4	11882
0.4-0.5	6089
0.5-0.6	4710
0.6-0.7	7013
0.7-0.8	4564
0.8-0.85	694
0.85-0.9	258
0.9-0.95	37
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC224161
0.9863	High Similarity	NPC279406
0.9863	High Similarity	NPC226809
0.9733	High Similarity	NPC471404
0.9733	High Similarity	NPC86630
0.9733	High Similarity	NPC151474
0.9733	High Similarity	NPC106601
0.9733	High Similarity	NPC159526
0.9733	High Similarity	NPC205613
0.9733	High Similarity	NPC212614
0.9667	High Similarity	NPC4809
0.9667	High Similarity	NPC147743
0.9667	High Similarity	NPC73517
0.9521	High Similarity	NPC262911
0.9521	High Similarity	NPC294558
0.9521	High Similarity	NPC82917
0.9521	High Similarity	NPC263940
0.9521	High Similarity	NPC70409
0.9521	High Similarity	NPC18185
0.9521	High Similarity	NPC236202
0.9521	High Similarity	NPC170103
0.9521	High Similarity	NPC58190
0.9521	High Similarity	NPC204770
0.9521	High Similarity	NPC108811
0.9521	High Similarity	NPC202742
0.9474	High Similarity	NPC185231
0.9459	High Similarity	NPC477612
0.9452	High Similarity	NPC96576
0.9392	High Similarity	NPC211561
0.9333	High Similarity	NPC46283
0.9333	High Similarity	NPC226108
0.9333	High Similarity	NPC44192
0.9333	High Similarity	NPC134911
0.9333	High Similarity	NPC469944
0.9333	High Similarity	NPC272552
0.9333	High Similarity	NPC322899
0.9324	High Similarity	NPC227516
0.9324	High Similarity	NPC20757
0.9267	High Similarity	NPC471403
0.9184	High Similarity	NPC171932
0.9184	High Similarity	NPC28440
0.9145	High Similarity	NPC306267
0.9145	High Similarity	NPC20050
0.911	High Similarity	NPC277331
0.911	High Similarity	NPC178054
0.911	High Similarity	NPC100482
0.9085	High Similarity	NPC157333
0.9067	High Similarity	NPC281549
0.9054	High Similarity	NPC475492
0.9045	High Similarity	NPC12326
0.9013	High Similarity	NPC329343
0.9013	High Similarity	NPC321972
0.9013	High Similarity	NPC324517
0.9013	High Similarity	NPC259707
0.9007	High Similarity	NPC318373
0.9007	High Similarity	NPC321657
0.8994	High Similarity	NPC9309
0.8933	High Similarity	NPC150714
0.8933	High Similarity	NPC260397
0.8933	High Similarity	NPC102280
0.8933	High Similarity	NPC248053
0.8933	High Similarity	NPC95652
0.8933	High Similarity	NPC155564
0.8917	High Similarity	NPC1253
0.8917	High Similarity	NPC100936
0.8912	High Similarity	NPC262189
0.8903	High Similarity	NPC202104
0.8889	High Similarity	NPC473621
0.8882	High Similarity	NPC470826
0.8882	High Similarity	NPC476969
0.8882	High Similarity	NPC473266
0.8882	High Similarity	NPC470098
0.8867	High Similarity	NPC181615
0.8854	High Similarity	NPC470828
0.8831	High Similarity	NPC59692
0.8816	High Similarity	NPC280945
0.88	High Similarity	NPC473108
0.88	High Similarity	NPC304894
0.88	High Similarity	NPC15659
0.879	High Similarity	NPC470827
0.8784	High Similarity	NPC22317
0.8784	High Similarity	NPC266197
0.8784	High Similarity	NPC291101
0.8776	High Similarity	NPC470308
0.8776	High Similarity	NPC470307
0.8776	High Similarity	NPC474390
0.875	High Similarity	NPC328567
0.875	High Similarity	NPC262297
0.875	High Similarity	NPC320970
0.875	High Similarity	NPC320671
0.875	High Similarity	NPC153182
0.875	High Similarity	NPC327412
0.875	High Similarity	NPC174251
0.8733	High Similarity	NPC173203
0.8733	High Similarity	NPC163508
0.8716	High Similarity	NPC260741
0.8716	High Similarity	NPC70682
0.871	High Similarity	NPC476391
0.871	High Similarity	NPC325860
0.871	High Similarity	NPC157783
0.8707	High Similarity	NPC470802
0.8707	High Similarity	NPC471522
0.8693	High Similarity	NPC329836
0.8693	High Similarity	NPC473876
0.8684	High Similarity	NPC215678
0.8684	High Similarity	NPC14468
0.8684	High Similarity	NPC324492
0.8684	High Similarity	NPC274454
0.8684	High Similarity	NPC317053
0.8671	High Similarity	NPC125495
0.8667	High Similarity	NPC59841
0.8667	High Similarity	NPC204347
0.8667	High Similarity	NPC475891
0.8667	High Similarity	NPC2613
0.8658	High Similarity	NPC61783
0.8658	High Similarity	NPC20520
0.8649	High Similarity	NPC211549
0.8645	High Similarity	NPC2745
0.8645	High Similarity	NPC302915
0.8639	High Similarity	NPC164787
0.8639	High Similarity	NPC473413
0.8627	High Similarity	NPC473480
0.8627	High Similarity	NPC474397
0.8627	High Similarity	NPC15538
0.8627	High Similarity	NPC101376
0.8616	High Similarity	NPC98083
0.8616	High Similarity	NPC94220
0.8616	High Similarity	NPC166456
0.8616	High Similarity	NPC24339
0.8616	High Similarity	NPC7543
0.8606	High Similarity	NPC98583
0.86	High Similarity	NPC263261
0.86	High Similarity	NPC470372
0.86	High Similarity	NPC471389
0.86	High Similarity	NPC87725
0.86	High Similarity	NPC35216
0.8599	High Similarity	NPC8712
0.8591	High Similarity	NPC32630
0.8591	High Similarity	NPC22517
0.859	High Similarity	NPC233467
0.8581	High Similarity	NPC195561
0.8581	High Similarity	NPC265433
0.8581	High Similarity	NPC302701
0.8581	High Similarity	NPC16435
0.8581	High Similarity	NPC270456
0.8581	High Similarity	NPC158784
0.8581	High Similarity	NPC162659
0.8581	High Similarity	NPC269091
0.8581	High Similarity	NPC306441
0.8581	High Similarity	NPC248727
0.8571	High Similarity	NPC476617
0.8571	High Similarity	NPC66840
0.8571	High Similarity	NPC256307
0.8571	High Similarity	NPC476615
0.8571	High Similarity	NPC476616
0.8562	High Similarity	NPC126291
0.8562	High Similarity	NPC61477
0.8562	High Similarity	NPC261619
0.8562	High Similarity	NPC185604
0.8562	High Similarity	NPC15658
0.8562	High Similarity	NPC78770
0.8562	High Similarity	NPC126029
0.8562	High Similarity	NPC219876
0.8553	High Similarity	NPC45257
0.8553	High Similarity	NPC63879
0.8553	High Similarity	NPC50250
0.8553	High Similarity	NPC168579
0.8553	High Similarity	NPC138227
0.8553	High Similarity	NPC93323
0.8553	High Similarity	NPC114119
0.8553	High Similarity	NPC470097
0.8553	High Similarity	NPC76176
0.8553	High Similarity	NPC280092
0.8553	High Similarity	NPC12641
0.8553	High Similarity	NPC469313
0.8553	High Similarity	NPC471415
0.8545	High Similarity	NPC65333
0.8545	High Similarity	NPC100251
0.8535	High Similarity	NPC470769
0.8533	High Similarity	NPC472091
0.8533	High Similarity	NPC472090
0.8533	High Similarity	NPC472092
0.8533	High Similarity	NPC259519
0.8533	High Similarity	NPC309124
0.8533	High Similarity	NPC184797
0.8514	High Similarity	NPC125579
0.8514	High Similarity	NPC47398
0.8514	High Similarity	NPC234333
0.8514	High Similarity	NPC61946
0.8514	High Similarity	NPC151224
0.8514	High Similarity	NPC470356
0.8514	High Similarity	NPC112939
0.8514	High Similarity	NPC474206
0.8514	High Similarity	NPC94750
0.8514	High Similarity	NPC121812
0.8514	High Similarity	NPC260898
0.8514	High Similarity	NPC112246
0.8509	High Similarity	NPC155754
0.8509	High Similarity	NPC124747
0.8509	High Similarity	NPC109061

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC46335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	443
0.1-0.2	906
0.2-0.3	2045
0.3-0.4	2753
0.4-0.5	1547
0.5-0.6	917
0.6-0.7	461
0.7-0.8	73
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8562	High Similarity	NPD1613	Approved
0.8562	High Similarity	NPD1612	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD4908	Phase 1
0.8108	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6166	Phase 2
0.7917	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD8455	Phase 2
0.7818	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1610	Phase 2
0.7733	Intermediate Similarity	NPD7074	Phase 3
0.7719	Intermediate Similarity	NPD7228	Approved
0.7697	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6674	Discontinued
0.763	Intermediate Similarity	NPD7472	Approved
0.7616	Intermediate Similarity	NPD2861	Phase 2
0.7582	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7054	Approved
0.7557	Intermediate Similarity	NPD8312	Approved
0.7557	Intermediate Similarity	NPD8313	Approved
0.7545	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7251	Discontinued
0.753	Intermediate Similarity	NPD1934	Approved
0.7529	Intermediate Similarity	NPD6959	Discontinued
0.7516	Intermediate Similarity	NPD4625	Phase 3
0.7514	Intermediate Similarity	NPD8053	Approved
0.7514	Intermediate Similarity	NPD8054	Approved
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD1653	Approved
0.7486	Intermediate Similarity	NPD6797	Phase 2
0.7471	Intermediate Similarity	NPD5844	Phase 1
0.7438	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.741	Intermediate Similarity	NPD4380	Phase 2
0.7371	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4749	Approved
0.7345	Intermediate Similarity	NPD7240	Approved
0.7326	Intermediate Similarity	NPD7199	Phase 2
0.7321	Intermediate Similarity	NPD37	Approved
0.7317	Intermediate Similarity	NPD7447	Phase 1
0.7312	Intermediate Similarity	NPD7266	Discontinued
0.7303	Intermediate Similarity	NPD8651	Approved
0.7294	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD7768	Phase 2
0.7294	Intermediate Similarity	NPD4965	Approved
0.7294	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD5494	Approved
0.7261	Intermediate Similarity	NPD4060	Phase 1
0.7256	Intermediate Similarity	NPD7213	Phase 3
0.7256	Intermediate Similarity	NPD7212	Phase 2
0.7216	Intermediate Similarity	NPD3818	Discontinued
0.7215	Intermediate Similarity	NPD5124	Phase 1
0.7215	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2801	Approved
0.7176	Intermediate Similarity	NPD1465	Phase 2
0.7175	Intermediate Similarity	NPD8156	Discontinued
0.7161	Intermediate Similarity	NPD3018	Phase 2
0.7159	Intermediate Similarity	NPD7473	Discontinued
0.7158	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1511	Approved
0.7152	Intermediate Similarity	NPD3620	Phase 2
0.7151	Intermediate Similarity	NPD7075	Discontinued
0.7151	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4538	Approved
0.7125	Intermediate Similarity	NPD4536	Approved
0.7125	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7097	Phase 1
0.7119	Intermediate Similarity	NPD8252	Approved
0.7119	Intermediate Similarity	NPD8099	Discontinued
0.7119	Intermediate Similarity	NPD8251	Approved
0.7111	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7549	Discontinued
0.7108	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1091	Approved
0.7097	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3787	Discontinued
0.7086	Intermediate Similarity	NPD6232	Discontinued
0.7081	Intermediate Similarity	NPD5588	Approved
0.7081	Intermediate Similarity	NPD5960	Phase 3
0.7076	Intermediate Similarity	NPD7819	Suspended
0.7068	Intermediate Similarity	NPD7680	Approved
0.7066	Intermediate Similarity	NPD1512	Approved
0.7056	Intermediate Similarity	NPD6559	Discontinued
0.7052	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8127	Discontinued
0.7013	Intermediate Similarity	NPD2983	Phase 2
0.7013	Intermediate Similarity	NPD2982	Phase 2
0.7011	Intermediate Similarity	NPD7906	Approved
0.7007	Intermediate Similarity	NPD7843	Approved
0.7	Intermediate Similarity	NPD5735	Approved
0.6995	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3882	Suspended
0.698	Remote Similarity	NPD7157	Approved
0.6977	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7466	Approved
0.6959	Remote Similarity	NPD7411	Suspended
0.6959	Remote Similarity	NPD5283	Phase 1
0.6959	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4663	Approved
0.6948	Remote Similarity	NPD2981	Phase 2
0.6947	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7041	Phase 2
0.6946	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3817	Phase 2
0.6933	Remote Similarity	NPD6099	Approved
0.6933	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1652	Phase 2
0.6905	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7229	Phase 3
0.689	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5763	Approved
0.689	Remote Similarity	NPD5762	Approved
0.689	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD8151	Discontinued
0.6886	Remote Similarity	NPD5058	Phase 3
0.6885	Remote Similarity	NPD7311	Approved
0.6885	Remote Similarity	NPD7313	Approved
0.6885	Remote Similarity	NPD4577	Approved
0.6885	Remote Similarity	NPD4578	Approved
0.6885	Remote Similarity	NPD7310	Approved
0.6885	Remote Similarity	NPD7312	Approved
0.6871	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8166	Discontinued
0.6867	Remote Similarity	NPD6671	Approved
0.6867	Remote Similarity	NPD3892	Phase 2
0.6863	Remote Similarity	NPD6516	Phase 2
0.6863	Remote Similarity	NPD5846	Approved
0.6848	Remote Similarity	NPD1549	Phase 2
0.6848	Remote Similarity	NPD7309	Approved
0.6842	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5402	Approved
0.6839	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3751	Discontinued
0.6826	Remote Similarity	NPD6190	Approved
0.6824	Remote Similarity	NPD228	Approved
0.6821	Remote Similarity	NPD6801	Discontinued
0.6816	Remote Similarity	NPD27	Approved
0.6816	Remote Similarity	NPD2489	Approved
0.6813	Remote Similarity	NPD6798	Discontinued
0.6809	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5177	Phase 3
0.6805	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3021	Approved
0.6803	Remote Similarity	NPD3022	Approved
0.6798	Remote Similarity	NPD3051	Approved
0.679	Remote Similarity	NPD6355	Discontinued
0.6772	Remote Similarity	NPD6584	Phase 3
0.6766	Remote Similarity	NPD6331	Phase 2
0.6766	Remote Similarity	NPD3750	Approved
0.676	Remote Similarity	NPD2969	Approved
0.676	Remote Similarity	NPD2970	Approved
0.675	Remote Similarity	NPD7095	Approved
0.6747	Remote Similarity	NPD2424	Discontinued
0.6747	Remote Similarity	NPD7037	Approved
0.6744	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD2684	Approved
0.6734	Remote Similarity	NPD7783	Phase 2
0.6734	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1558	Phase 1
0.6726	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2677	Approved
0.6725	Remote Similarity	NPD5403	Approved
0.6706	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4678	Approved
0.6705	Remote Similarity	NPD4675	Approved
0.6688	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5327	Phase 3
0.6687	Remote Similarity	NPD3540	Phase 1
0.6686	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD6072	Discontinued
0.6667	Remote Similarity	NPD7831	Phase 2
0.6667	Remote Similarity	NPD290	Approved
0.6667	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD7833	Phase 2
0.6667	Remote Similarity	NPD4535	Phase 3
0.6667	Remote Similarity	NPD422	Phase 1
0.6647	Remote Similarity	NPD4005	Discontinued
0.6647	Remote Similarity	NPD7390	Discontinued
0.6646	Remote Similarity	NPD6696	Suspended
0.6629	Remote Similarity	NPD5722	Discontinued
0.6628	Remote Similarity	NPD2122	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data