NPASS Compound

Structure

CID190939 OpenBabel06191715572D 96105 0 0 1 0 0 0 0 0999 V2000 0.3889 8.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3889 8.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1139 5.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0628 3.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1114 8.0415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6396 3.8070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2329 4.7205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0069 7.0470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6561 4.1206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2493 5.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4586 2.0844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2384 6.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4696 2.2935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6341 13.0141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6621 -2.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2567 -2.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 -1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 3.4407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4069 9.6238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2567 -4.4237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3024 8.6293 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2843 7.2280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0519 2.9980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2384 4.8250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6506 4.0160 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8317 5.7386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0933 6.6402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4952 7.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8763 1.3799 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4054 -4.9153 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8708 1.2754 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7205 12.6074 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6621 -1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2567 -1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9831 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.9492 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6292 6.8213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5540 -4.4237 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9115 13.1951 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5135 -0.9831 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1081 -0.9831 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8513 -1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0020 12.7884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5135 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8513 1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5540 -3.4407 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1066 11.7939 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6621 0.4915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7027 1.9661 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2567 0.4915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.9661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1081 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7027 -0.9831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7027 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7024 11.2061 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4054 -2.9492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7027 2.9492 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8108 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4054 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8513 0.4915 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8371 5.8431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0573 3.1025 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7386 14.0086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5135 -2.9492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1081 -2.9492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 -2.4576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7027 2.9492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9888 5.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5998 8.3158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2885 0.5709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4054 -5.8983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7027 -4.9153 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0160 14.1897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3648 -1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9594 -1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 -2.4576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8111 13.3762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3648 0.4915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 0.4915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7027 -2.9492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0201 11.3871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6621 1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5540 1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2567 1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5979 10.2116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2567 -3.4407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5540 3.4407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6160 11.6128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8108 -0.9831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4054 -0.9831 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 -0.8513 3.4407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9594 0.4915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4054 -1.9661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5540 0.4915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 5 8 1 0 0 0 0 5 21 1 0 0 0 0 6 7 1 0 0 0 0 6 23 2 0 0 0 0 8 27 1 0 0 0 0 9 10 1 0 0 0 0 9 25 1 0 0 0 0 10 61 1 0 0 0 0 11 23 1 0 0 0 0 11 31 1 0 0 0 0 12 26 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 13 62 1 0 0 0 0 14 63 1 0 0 0 0 15 64 1 0 0 0 0 16 65 1 0 0 0 0 17 66 1 0 0 0 0 18 67 1 0 0 0 0 19 21 1 0 0 0 0 19 85 1 0 0 0 0 20 30 1 0 0 0 0 20 86 1 0 0 0 0 21 1 1 1 0 0 0 22 27 1 0 0 0 0 22 37 2 0 0 0 0 23 62 1 0 0 0 0 24 7 1 1 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 25 62 1 6 0 0 0 26 61 1 6 0 0 0 27 68 2 0 0 0 0 28 37 1 0 0 0 0 28 69 2 0 0 0 0 29 31 1 0 0 0 0 29 70 1 1 0 0 0 30 38 1 0 0 0 0 30 71 1 1 0 0 0 31 87 1 6 0 0 0 32 14 1 1 0 0 0 32 39 1 0 0 0 0 32 88 1 0 0 0 0 33 15 1 1 0 0 0 33 40 1 0 0 0 0 33 89 1 0 0 0 0 34 16 1 1 0 0 0 34 41 1 0 0 0 0 34 90 1 0 0 0 0 35 17 1 1 0 0 0 35 42 1 0 0 0 0 35 91 1 0 0 0 0 36 18 1 6 0 0 0 36 51 1 0 0 0 0 36 92 1 0 0 0 0 37 61 1 0 0 0 0 38 46 1 0 0 0 0 38 72 1 6 0 0 0 39 43 1 0 0 0 0 39 73 1 6 0 0 0 40 44 1 0 0 0 0 40 74 1 6 0 0 0 41 52 1 0 0 0 0 41 75 1 6 0 0 0 42 53 1 0 0 0 0 42 76 1 6 0 0 0 43 47 1 0 0 0 0 43 77 1 1 0 0 0 44 48 1 0 0 0 0 44 78 1 1 0 0 0 45 49 1 0 0 0 0 45 51 1 0 0 0 0 45 79 1 6 0 0 0 46 56 1 0 0 0 0 46 80 1 1 0 0 0 47 55 1 0 0 0 0 47 81 1 6 0 0 0 48 58 1 0 0 0 0 48 82 1 6 0 0 0 49 57 1 0 0 0 0 49 83 1 1 0 0 0 50 52 1 0 0 0 0 50 59 1 0 0 0 0 50 84 1 6 0 0 0 51 93 1 6 0 0 0 52 94 1 1 0 0 0 53 54 1 0 0 0 0 53 95 1 1 0 0 0 54 60 1 0 0 0 0 54 96 1 6 0 0 0 55 85 1 1 0 0 0 55 88 1 0 0 0 0 56 86 1 0 0 0 0 56 95 1 6 0 0 0 57 87 1 6 0 0 0 57 92 1 0 0 0 0 58 89 1 0 0 0 0 58 94 1 1 0 0 0 59 90 1 0 0 0 0 59 96 1 1 0 0 0 60 91 1 0 0 0 0 60 93 1 1 0 0 0 61 3 1 6 0 0 0 62 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1386.59
Volume:	1283.665
LogP:	-1.861
LogD:	-3.047
LogS:	-2.253
# Rotatable Bonds:	22
TPSA:	549.5
# H-Bond Aceptor:	34
# H-Bond Donor:	20
# Rings:	10
# Heavy Atoms:	34

MedChem Properties

QED Drug-Likeness Score:	0.045
Synthetic Accessibility Score:	7.835
Fsp3:	0.903
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.476
MDCK Permeability:	0.0007368501974269748
Pgp-inhibitor:	0.0
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.315
Plasma Protein Binding (PPB):	49.96931457519531%
Volume Distribution (VD):	-0.499
Pgp-substrate:	23.315452575683594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.038
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.001
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-0.513
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.384
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.296
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.012
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.004

Download Data

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

Natural Product: NPC190939

Natural Product ID:	NPC190939
*Common Name:**	(25R)-3Beta-[(O-Beta-D-Glucopyranosyl-(1->3)-O-Beta-D-Glucopyranosyl-(1->2)-O-[Beta-D-Xylopyranosyl-(1->3)]-O-Beta-D-Glucopyranosyl-(1->4)-Beta-D-Galactopyranosyl)-Oxy]-26-[(Beta-D-Glucopyranosyl)Oxy]-2Alpha-Hydroxycholesta-5,17-Diene-16,22-Dione
IUPAC Name:	(2R,3R,8R,9S,10R,13S,14S,17Z)-3-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-10,13-dimethyl-17-[(6R)-6-methyl-3-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-ylidene]-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-16-one
Synonyms:
Standard InCHIKey:	PIACQCAHKHMXIA-QACVDFGUSA-N
Standard InCHI:	InChI=1S/C62H98O34/c1-21(19-85-55-47(81)43(77)39(73)32(14-63)88-55)5-8-27(68)22(2)37-28(69)12-26-24-7-6-23-11-31(29(70)13-62(23,4)25(24)9-10-61(26,37)3)87-57-49(83)45(79)51(36(18-67)92-57)93-60-54(53(42(76)35(17-66)91-60)95-56-46(80)38(72)30(71)20-86-56)96-59-50(84)52(41(75)34(16-65)90-59)94-58-48(82)44(78)40(74)33(15-64)89-58/h6,21,24-26,29-36,38-60,63-67,70-84H,5,7-20H2,1-4H3/b37-22+/t21-,24-,25+,26+,29-,30-,31-,32-,33-,34-,35-,36-,38+,39-,40-,41-,42-,43+,44+,45-,46-,47-,48-,49-,50-,51+,52+,53+,54-,55-,56+,57-,58+,59+,60+,61+,62+/m1/s1
SMILES:	C[C@H](CCC(=O)/C(=C/1C(=O)C[C@H]2[C@@H]3CC=C4C[C@H]([C@@H](C[C@]4(C)[C@H]3CC[C@]12C)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)/C)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506498
PubChem CID:	11007753
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[11170659]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12502329]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27323	Cestrum nocturnum	Species	Solanaceae	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
LD50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	LD50	=	281.0	ug ml-1	PMID[501367]

☑ 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 NPC190939 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	264
0.1-0.2	1666
0.2-0.3	5105
0.3-0.4	10878
0.4-0.5	10478
0.5-0.6	6646
0.6-0.7	4499
0.7-0.8	1812
0.8-0.85	793
0.85-0.9	510
0.9-0.95	43
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC197003
0.9554	High Similarity	NPC308459
0.9381	High Similarity	NPC129393
0.9298	High Similarity	NPC476675
0.9224	High Similarity	NPC248202
0.9224	High Similarity	NPC473505
0.9196	High Similarity	NPC279638
0.9107	High Similarity	NPC165439
0.9052	High Similarity	NPC305771
0.9052	High Similarity	NPC169816
0.9052	High Similarity	NPC15918
0.9052	High Similarity	NPC94072
0.9	High Similarity	NPC246205
0.8974	High Similarity	NPC256983
0.8966	High Similarity	NPC249553
0.8966	High Similarity	NPC476672
0.8966	High Similarity	NPC182900
0.8966	High Similarity	NPC475182
0.8957	High Similarity	NPC473401
0.8947	High Similarity	NPC477252
0.8938	High Similarity	NPC102088
0.8929	High Similarity	NPC474265
0.8929	High Similarity	NPC210420
0.8879	High Similarity	NPC476670
0.887	High Similarity	NPC470514
0.887	High Similarity	NPC470513
0.885	High Similarity	NPC62696
0.885	High Similarity	NPC293038
0.885	High Similarity	NPC260665
0.8824	High Similarity	NPC476673
0.8803	High Similarity	NPC476543
0.8803	High Similarity	NPC476544
0.8803	High Similarity	NPC476545
0.8793	High Similarity	NPC477464
0.8793	High Similarity	NPC161738
0.8783	High Similarity	NPC148417
0.8783	High Similarity	NPC110633
0.8783	High Similarity	NPC309433
0.8783	High Similarity	NPC136768
0.8772	High Similarity	NPC57484
0.8772	High Similarity	NPC76972
0.8772	High Similarity	NPC123199
0.8772	High Similarity	NPC71065
0.8772	High Similarity	NPC293330
0.8772	High Similarity	NPC475140
0.8772	High Similarity	NPC474557
0.8772	High Similarity	NPC471385
0.8772	High Similarity	NPC79643
0.8772	High Similarity	NPC294453
0.8772	High Similarity	NPC261506
0.8772	High Similarity	NPC54636
0.8772	High Similarity	NPC298034
0.8772	High Similarity	NPC475160
0.8772	High Similarity	NPC202828
0.8772	High Similarity	NPC473882
0.8772	High Similarity	NPC41061
0.8772	High Similarity	NPC469782
0.8772	High Similarity	NPC204414
0.8772	High Similarity	NPC224381
0.8772	High Similarity	NPC305981
0.8772	High Similarity	NPC309907
0.8772	High Similarity	NPC227551
0.8772	High Similarity	NPC471550
0.8772	High Similarity	NPC65105
0.8772	High Similarity	NPC236638
0.8772	High Similarity	NPC250247
0.8772	High Similarity	NPC74727
0.8772	High Similarity	NPC70809
0.8772	High Similarity	NPC4328
0.8772	High Similarity	NPC476068
0.8772	High Similarity	NPC43550
0.8772	High Similarity	NPC60557
0.8772	High Similarity	NPC119592
0.8772	High Similarity	NPC161717
0.8772	High Similarity	NPC100639
0.8772	High Similarity	NPC473714
0.8772	High Similarity	NPC67857
0.8761	High Similarity	NPC477253
0.875	High Similarity	NPC475317
0.875	High Similarity	NPC154856
0.875	High Similarity	NPC52241
0.8739	High Similarity	NPC473474
0.8739	High Similarity	NPC476674
0.8718	High Similarity	NPC475187
0.8707	High Similarity	NPC237191
0.8707	High Similarity	NPC475899
0.8707	High Similarity	NPC36831
0.8699	High Similarity	NPC102015
0.8696	High Similarity	NPC471384
0.8696	High Similarity	NPC472718
0.8696	High Similarity	NPC161674
0.8684	High Similarity	NPC133818
0.8684	High Similarity	NPC323341
0.8684	High Similarity	NPC174720
0.8684	High Similarity	NPC241909
0.8684	High Similarity	NPC192600
0.8684	High Similarity	NPC251263
0.8684	High Similarity	NPC295823
0.8684	High Similarity	NPC114304
0.8684	High Similarity	NPC114287
0.8684	High Similarity	NPC155410
0.8684	High Similarity	NPC150400
0.8684	High Similarity	NPC46665
0.8684	High Similarity	NPC124296
0.8684	High Similarity	NPC134835
0.8684	High Similarity	NPC166422
0.8684	High Similarity	NPC475287
0.8684	High Similarity	NPC151543
0.8684	High Similarity	NPC473826
0.8684	High Similarity	NPC96641
0.8684	High Similarity	NPC73318
0.8684	High Similarity	NPC251309
0.8684	High Similarity	NPC475467
0.8684	High Similarity	NPC163183
0.8684	High Similarity	NPC473343
0.8684	High Similarity	NPC219180
0.8684	High Similarity	NPC258885
0.8684	High Similarity	NPC309714
0.8673	High Similarity	NPC263827
0.8673	High Similarity	NPC250481
0.8673	High Similarity	NPC285410
0.8661	High Similarity	NPC302057
0.8655	High Similarity	NPC160084
0.8655	High Similarity	NPC476542
0.8644	High Similarity	NPC293031
0.8644	High Similarity	NPC477463
0.8644	High Similarity	NPC275225
0.8644	High Similarity	NPC68767
0.8644	High Similarity	NPC51099
0.8632	High Similarity	NPC471577
0.8621	High Similarity	NPC69811
0.8621	High Similarity	NPC191827
0.8621	High Similarity	NPC473452
0.8621	High Similarity	NPC475209
0.8621	High Similarity	NPC68175
0.8621	High Similarity	NPC470876
0.8621	High Similarity	NPC104137
0.8621	High Similarity	NPC309223
0.8621	High Similarity	NPC102505
0.8621	High Similarity	NPC123522
0.8621	High Similarity	NPC8524
0.8621	High Similarity	NPC286457
0.8621	High Similarity	NPC475514
0.8621	High Similarity	NPC220160
0.8621	High Similarity	NPC471580
0.8621	High Similarity	NPC85154
0.8621	High Similarity	NPC33012
0.8621	High Similarity	NPC185466
0.8618	High Similarity	NPC473805
0.8618	High Similarity	NPC473519
0.8596	High Similarity	NPC139044
0.8596	High Similarity	NPC139894
0.8596	High Similarity	NPC473383
0.8596	High Similarity	NPC104071
0.8596	High Similarity	NPC475516
0.8596	High Similarity	NPC324875
0.8596	High Similarity	NPC102439
0.8596	High Similarity	NPC31896
0.8596	High Similarity	NPC263359
0.8596	High Similarity	NPC471967
0.8596	High Similarity	NPC104400
0.8596	High Similarity	NPC257468
0.8596	High Similarity	NPC475504
0.8596	High Similarity	NPC130427
0.8596	High Similarity	NPC233003
0.8596	High Similarity	NPC32361
0.8596	High Similarity	NPC292677
0.8596	High Similarity	NPC109079
0.8596	High Similarity	NPC469946
0.8596	High Similarity	NPC101744
0.8596	High Similarity	NPC473373
0.8596	High Similarity	NPC244431
0.8596	High Similarity	NPC471383
0.8596	High Similarity	NPC210569
0.8596	High Similarity	NPC10320
0.8596	High Similarity	NPC79718
0.8596	High Similarity	NPC276093
0.8571	High Similarity	NPC295389
0.8571	High Similarity	NPC156789
0.8571	High Similarity	NPC28532
0.8559	High Similarity	NPC37860
0.8559	High Similarity	NPC153673
0.8559	High Similarity	NPC476991
0.8559	High Similarity	NPC142151
0.8559	High Similarity	NPC210178
0.8559	High Similarity	NPC144644
0.8559	High Similarity	NPC110385
0.8559	High Similarity	NPC267694
0.8559	High Similarity	NPC268184
0.8547	High Similarity	NPC475632
0.8547	High Similarity	NPC86020
0.8537	High Similarity	NPC241008
0.8534	High Similarity	NPC26626
0.8534	High Similarity	NPC160415
0.8534	High Similarity	NPC305267
0.8534	High Similarity	NPC51465
0.8534	High Similarity	NPC476992
0.8534	High Similarity	NPC75287
0.8534	High Similarity	NPC58448
0.8534	High Similarity	NPC288205

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 NPC190939 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	1912
0.2-0.3	4063
0.3-0.4	1946
0.4-0.5	525
0.5-0.6	259
0.6-0.7	165
0.7-0.8	39
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8649	High Similarity	NPD6412	Phase 2
0.8347	Intermediate Similarity	NPD8328	Phase 3
0.8174	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8051	Intermediate Similarity	NPD8133	Approved
0.7851	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD8294	Approved
0.7805	Intermediate Similarity	NPD8377	Approved
0.7778	Intermediate Similarity	NPD7507	Approved
0.7778	Intermediate Similarity	NPD6686	Approved
0.7742	Intermediate Similarity	NPD8378	Approved
0.7742	Intermediate Similarity	NPD8033	Approved
0.7742	Intermediate Similarity	NPD8296	Approved
0.7742	Intermediate Similarity	NPD8380	Approved
0.7742	Intermediate Similarity	NPD8379	Approved
0.7742	Intermediate Similarity	NPD8335	Approved
0.768	Intermediate Similarity	NPD6370	Approved
0.7672	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD7736	Approved
0.7597	Intermediate Similarity	NPD7319	Approved
0.7578	Intermediate Similarity	NPD8293	Discontinued
0.752	Intermediate Similarity	NPD6059	Approved
0.752	Intermediate Similarity	NPD6054	Approved
0.746	Intermediate Similarity	NPD8516	Approved
0.746	Intermediate Similarity	NPD8515	Approved
0.746	Intermediate Similarity	NPD8517	Approved
0.744	Intermediate Similarity	NPD7516	Approved
0.7377	Intermediate Similarity	NPD6882	Approved
0.7377	Intermediate Similarity	NPD8297	Approved
0.736	Intermediate Similarity	NPD7328	Approved
0.736	Intermediate Similarity	NPD7327	Approved
0.7344	Intermediate Similarity	NPD6067	Discontinued
0.7323	Intermediate Similarity	NPD7503	Approved
0.7323	Intermediate Similarity	NPD6015	Approved
0.7323	Intermediate Similarity	NPD8513	Phase 3
0.7323	Intermediate Similarity	NPD6016	Approved
0.7287	Intermediate Similarity	NPD7492	Approved
0.728	Intermediate Similarity	NPD6009	Approved
0.7266	Intermediate Similarity	NPD5988	Approved
0.7244	Intermediate Similarity	NPD6319	Approved
0.7231	Intermediate Similarity	NPD6616	Approved
0.7193	Intermediate Similarity	NPD7748	Approved
0.7177	Intermediate Similarity	NPD4632	Approved
0.7176	Intermediate Similarity	NPD7078	Approved
0.7167	Intermediate Similarity	NPD6402	Approved
0.7167	Intermediate Similarity	NPD5739	Approved
0.7167	Intermediate Similarity	NPD7128	Approved
0.7167	Intermediate Similarity	NPD6675	Approved
0.7155	Intermediate Similarity	NPD7902	Approved
0.7154	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5328	Approved
0.7131	Intermediate Similarity	NPD6373	Approved
0.7131	Intermediate Similarity	NPD6372	Approved
0.7105	Intermediate Similarity	NPD6399	Phase 3
0.7049	Intermediate Similarity	NPD7320	Approved
0.7049	Intermediate Similarity	NPD6881	Approved
0.7049	Intermediate Similarity	NPD6899	Approved
0.7027	Intermediate Similarity	NPD3618	Phase 1
0.7018	Intermediate Similarity	NPD6079	Approved
0.7018	Intermediate Similarity	NPD7515	Phase 2
0.7016	Intermediate Similarity	NPD8130	Phase 1
0.7016	Intermediate Similarity	NPD6650	Approved
0.7016	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD4755	Approved
0.7008	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD4786	Approved
0.6992	Remote Similarity	NPD6033	Approved
0.6985	Remote Similarity	NPD8450	Suspended
0.6972	Remote Similarity	NPD3667	Approved
0.6967	Remote Similarity	NPD5701	Approved
0.6967	Remote Similarity	NPD5697	Approved
0.6957	Remote Similarity	NPD8171	Discontinued
0.6949	Remote Similarity	NPD7638	Approved
0.6935	Remote Similarity	NPD7290	Approved
0.6935	Remote Similarity	NPD4634	Approved
0.6935	Remote Similarity	NPD6883	Approved
0.6935	Remote Similarity	NPD7102	Approved
0.6912	Remote Similarity	NPD8449	Approved
0.6897	Remote Similarity	NPD7900	Approved
0.6897	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7640	Approved
0.6891	Remote Similarity	NPD7639	Approved
0.6891	Remote Similarity	NPD4696	Approved
0.6891	Remote Similarity	NPD4700	Approved
0.6891	Remote Similarity	NPD5286	Approved
0.6891	Remote Similarity	NPD5285	Approved
0.6885	Remote Similarity	NPD6008	Approved
0.688	Remote Similarity	NPD6847	Approved
0.688	Remote Similarity	NPD6617	Approved
0.688	Remote Similarity	NPD6869	Approved
0.6864	Remote Similarity	NPD6083	Phase 2
0.6864	Remote Similarity	NPD6084	Phase 2
0.6855	Remote Similarity	NPD6014	Approved
0.6855	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6013	Approved
0.6855	Remote Similarity	NPD6012	Approved
0.6847	Remote Similarity	NPD3665	Phase 1
0.6847	Remote Similarity	NPD3666	Approved
0.6847	Remote Similarity	NPD3133	Approved
0.6818	Remote Similarity	NPD7604	Phase 2
0.681	Remote Similarity	NPD4202	Approved
0.6794	Remote Similarity	NPD5983	Phase 2
0.678	Remote Similarity	NPD5221	Approved
0.678	Remote Similarity	NPD4697	Phase 3
0.678	Remote Similarity	NPD5222	Approved
0.678	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5225	Approved
0.6777	Remote Similarity	NPD4633	Approved
0.6777	Remote Similarity	NPD5226	Approved
0.6777	Remote Similarity	NPD5224	Approved
0.6777	Remote Similarity	NPD5211	Phase 2
0.6774	Remote Similarity	NPD6011	Approved
0.6754	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4767	Approved
0.6748	Remote Similarity	NPD4768	Approved
0.6746	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6684	Approved
0.6726	Remote Similarity	NPD5330	Approved
0.6726	Remote Similarity	NPD7521	Approved
0.6726	Remote Similarity	NPD7334	Approved
0.6726	Remote Similarity	NPD6409	Approved
0.6726	Remote Similarity	NPD7146	Approved
0.6723	Remote Similarity	NPD5173	Approved
0.6721	Remote Similarity	NPD5175	Approved
0.6721	Remote Similarity	NPD5174	Approved
0.6716	Remote Similarity	NPD6336	Discontinued
0.6696	Remote Similarity	NPD4753	Phase 2
0.6694	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5141	Approved
0.664	Remote Similarity	NPD4730	Approved
0.664	Remote Similarity	NPD4729	Approved
0.664	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8336	Approved
0.6618	Remote Similarity	NPD8337	Approved
0.6609	Remote Similarity	NPD6672	Approved
0.6609	Remote Similarity	NPD5737	Approved
0.6609	Remote Similarity	NPD6903	Approved
0.6585	Remote Similarity	NPD4754	Approved
0.6581	Remote Similarity	NPD8034	Phase 2
0.6581	Remote Similarity	NPD8035	Phase 2
0.6555	Remote Similarity	NPD5695	Phase 3
0.6549	Remote Similarity	NPD3668	Phase 3
0.6538	Remote Similarity	NPD6274	Approved
0.6535	Remote Similarity	NPD5247	Approved
0.6535	Remote Similarity	NPD5248	Approved
0.6535	Remote Similarity	NPD5250	Approved
0.6535	Remote Similarity	NPD5251	Approved
0.6535	Remote Similarity	NPD5249	Phase 3
0.6529	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD5956	Approved
0.6515	Remote Similarity	NPD7101	Approved
0.6515	Remote Similarity	NPD7100	Approved
0.6508	Remote Similarity	NPD5128	Approved
0.6496	Remote Similarity	NPD46	Approved
0.6496	Remote Similarity	NPD6698	Approved
0.6441	Remote Similarity	NPD6411	Approved
0.6439	Remote Similarity	NPD6335	Approved
0.6435	Remote Similarity	NPD5279	Phase 3
0.6434	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8338	Approved
0.6423	Remote Similarity	NPD8074	Phase 3
0.6418	Remote Similarity	NPD6908	Approved
0.6418	Remote Similarity	NPD6909	Approved
0.6417	Remote Similarity	NPD5210	Approved
0.6417	Remote Similarity	NPD4629	Approved
0.6412	Remote Similarity	NPD6868	Approved
0.6393	Remote Similarity	NPD4225	Approved
0.6379	Remote Similarity	NPD3573	Approved
0.6379	Remote Similarity	NPD7524	Approved
0.6372	Remote Similarity	NPD4221	Approved
0.6372	Remote Similarity	NPD4223	Phase 3
0.6371	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD6317	Approved
0.6357	Remote Similarity	NPD5216	Approved
0.6357	Remote Similarity	NPD5217	Approved
0.6357	Remote Similarity	NPD5215	Approved
0.6348	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5329	Approved
0.6316	Remote Similarity	NPD6314	Approved
0.6316	Remote Similarity	NPD6313	Approved
0.6309	Remote Similarity	NPD7625	Phase 1
0.6293	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5169	Approved
0.6279	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5135	Approved
0.6271	Remote Similarity	NPD6080	Approved
0.6271	Remote Similarity	NPD6904	Approved
0.6271	Remote Similarity	NPD6101	Approved
0.6271	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6673	Approved
0.6261	Remote Similarity	NPD4197	Approved
0.626	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD5168	Approved
0.625	Remote Similarity	NPD8080	Discontinued
0.6241	Remote Similarity	NPD7260	Phase 2
0.6231	Remote Similarity	NPD5127	Approved

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