NPASS Compound

Structure

NPC10039 OpenBabel06302215422D 103114 0 0 1 0 0 0 0 0999 V2000 1.1933 -1.1933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2522 -0.9412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4368 -1.6301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3780 -1.3780 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6301 -0.4368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9412 0.2522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1933 1.1933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5044 1.8823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7565 2.8235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6977 3.0757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9499 4.0168 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2609 4.7058 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3198 4.4536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0676 3.5125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3692 5.1426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2515 4.6382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6295 6.0162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5037 3.6971 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5037 2.7227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3475 2.2355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1914 2.7227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1657 2.7227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6785 1.8789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1914 3.6971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3475 4.1842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3475 5.1586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1914 5.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1914 6.6201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3475 7.1073 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3475 8.0817 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1914 7.5945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1914 8.5689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1914 9.5432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3475 10.0304 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5037 9.5432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5294 9.5432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0165 10.3870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5037 8.5689 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6599 8.0817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 7.1073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5037 6.6201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8161 5.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5037 5.6458 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6599 6.1330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 5.1586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 4.1842 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8161 3.6971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3475 11.0048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5037 11.4919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5037 12.4663 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6599 12.9535 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8161 12.4663 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8161 11.4919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0277 11.0048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8716 11.4919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7154 11.0048 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7154 10.0304 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5592 9.5432 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4030 10.0304 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4030 11.0048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5592 11.4919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2468 9.5432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5592 8.5689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8716 9.5432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 11.0048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0277 12.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 13.9278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3475 12.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5131 5.6470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4543 5.8991 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7064 6.8403 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6476 7.0925 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3366 6.4035 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0844 5.4623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7734 4.7734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1432 5.2102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2777 6.6557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9667 5.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9079 6.2189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5968 5.5299 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3447 4.5888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4035 4.3366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7145 5.0255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0336 3.8998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5380 5.7821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2270 5.0931 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1681 5.3453 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8571 4.6563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6049 3.7152 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6638 3.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9748 4.1520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2939 3.0262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7983 4.9085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4203 6.2865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1600 7.1600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8998 8.0336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0175 7.5293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8910 4.2690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3867 2.3867 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 -2.5713 -0.1846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0669 -2.0669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1846 -2.5713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 0 0 0 2 3 1 0 0 0 0 2100 1 0 0 0 0 3 4 1 0 0 0 0 3103 1 6 0 0 0 4 5 1 0 0 0 0 4102 1 1 0 0 0 5 6 1 0 0 0 0 5101 1 6 0 0 0 6 7 1 1 0 0 0 6100 1 0 0 0 0 7 8 1 0 0 0 0 9 8 1 1 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 99 1 6 0 0 0 11 12 1 0 0 0 0 11 98 1 1 0 0 0 12 13 1 0 0 0 0 12 69 1 6 0 0 0 13 14 1 0 0 0 0 13 15 1 1 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 18 16 1 6 0 0 0 18 25 1 0 0 0 0 18 46 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 25 24 1 6 0 0 0 25 26 1 0 0 0 0 26 43 1 0 0 0 0 26 27 2 0 0 0 0 27 28 1 0 0 0 0 29 28 1 6 0 0 0 29 30 1 0 0 0 0 29 41 1 0 0 0 0 30 38 1 0 0 0 0 30 31 1 6 0 0 0 30 32 1 0 0 0 0 32 33 1 0 0 0 0 33 34 1 0 0 0 0 34 35 1 0 0 0 0 34 48 1 1 0 0 0 35 36 1 0 0 0 0 35 37 1 0 0 0 0 35 38 1 0 0 0 0 38 39 1 1 0 0 0 39 40 1 0 0 0 0 40 41 1 0 0 0 0 41 42 1 6 0 0 0 41 43 1 0 0 0 0 43 44 1 6 0 0 0 43 45 1 0 0 0 0 45 46 1 0 0 0 0 46 47 1 1 0 0 0 49 48 1 1 0 0 0 49 50 1 0 0 0 0 49 65 1 0 0 0 0 50 51 1 0 0 0 0 50 68 1 6 0 0 0 51 52 1 0 0 0 0 51 67 1 1 0 0 0 52 53 1 0 0 0 0 52 66 1 6 0 0 0 53 54 1 1 0 0 0 53 65 1 0 0 0 0 54 55 1 0 0 0 0 56 55 1 6 0 0 0 56 57 1 0 0 0 0 56 61 1 0 0 0 0 57 58 1 0 0 0 0 57 64 1 1 0 0 0 58 59 1 0 0 0 0 58 63 1 6 0 0 0 59 60 1 0 0 0 0 59 62 1 1 0 0 0 60 61 1 0 0 0 0 70 69 1 1 0 0 0 70 71 1 0 0 0 0 70 76 1 0 0 0 0 71 72 1 0 0 0 0 71 97 1 6 0 0 0 72 73 1 0 0 0 0 72 96 1 1 0 0 0 73 74 1 0 0 0 0 73 77 1 6 0 0 0 74 75 1 1 0 0 0 74 76 1 0 0 0 0 78 77 1 1 0 0 0 78 79 1 0 0 0 0 78 83 1 0 0 0 0 79 80 1 0 0 0 0 79 95 1 6 0 0 0 80 81 1 0 0 0 0 80 85 1 1 0 0 0 81 82 1 0 0 0 0 81 84 1 6 0 0 0 82 83 1 0 0 0 0 86 85 1 1 0 0 0 86 87 1 0 0 0 0 86 91 1 0 0 0 0 87 88 1 0 0 0 0 87 94 1 6 0 0 0 88 89 1 0 0 0 0 88 93 1 1 0 0 0 89 90 1 0 0 0 0 89 92 1 6 0 0 0 90 91 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1484.7
Volume:	1392.897
LogP:	1.085
LogD:	1.166
LogS:	-3.31
# Rotatable Bonds:	17
TPSA:	530.66
# H-Bond Aceptor:	34
# H-Bond Donor:	19
# Rings:	12
# Heavy Atoms:	34

MedChem Properties

QED Drug-Likeness Score:	0.039
Synthetic Accessibility Score:	5.666
Fsp3:	0.957
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:	-6.163
MDCK Permeability:	0.000670496781822294
Pgp-inhibitor:	0.002
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.405
Plasma Protein Binding (PPB):	47.942893981933594%
Volume Distribution (VD):	-0.573
Pgp-substrate:	24.630273818969727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-1.339
Half-life (T1/2):	0.684

ADMET: Toxicity

hERG Blockers:	0.204
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.004
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.091
Carcinogencity:	0.131
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC10039

Natural Product ID:	NPC10039
*Common Name:**	CKBVDWQFFMQIGU-BTQDERTESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CKBVDWQFFMQIGU-BTQDERTESA-N
Standard InCHI:	InChI=1S/C69H112O34/c1-25-38(74)43(79)49(85)57(95-25)94-24-33-42(78)45(81)55(102-60-51(87)46(82)53(26(2)96-60)100-59-52(88)54(31(72)22-92-59)101-58-48(84)40(76)30(71)21-91-58)62(98-33)103-63(89)69-17-16-64(3,4)18-28(69)27-10-11-35-66(7)14-13-37(65(5,6)34(66)12-15-67(35,8)68(27,9)19-36(69)73)99-61-50(86)44(80)41(77)32(97-61)23-93-56-47(83)39(75)29(70)20-90-56/h10,25-26,28-62,70-88H,11-24H2,1-9H3/t25-,26-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37-,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+,66+,67-,68+,69-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](OC[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)OC(=O)[C@@]23CCC(C)(C)C[C@H]2C2=CC[C@H]4[C@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@]4(C)[C@]2(C)C[C@@H]3O)O[C@@H]2[C@H]([C@@H]([C@H]([C@H](CO[C@@H]3[C@H]([C@@H]([C@H](CO3)O)O)O)O2)O)O)O)O[C@@H]2[C@H]([C@@H]([C@H]([C@H](C)O2)O[C@@H]2[C@H]([C@@H]([C@H](CO2)O)O[C@@H]2[C@H]([C@@H]([C@H](CO2)O)O)O)O)O)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568781]
NPO8649	Drechslera gigantea	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16506833]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21341711]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21341711]
NPO3542	Eucomis punctata	Species	Hyacinthaceae	Eukaryota	n.a.	bulb	n.a.	PMID[21510636]
NPO2028	Campsis grandiflora	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2028	Campsis grandiflora	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2028	Campsis grandiflora	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6560	Laurus azorica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO379	Cunila spicata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2028	Campsis grandiflora	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9490	Thomandersia laurifolia	Species	Thomandersiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3542	Eucomis punctata	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3156	Rubus parvifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8487	Potentilla griffithii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10270	Rhododendron caucasicum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8649	Drechslera gigantea	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9872	Nerine filifolia	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4905	Peltogyne paniculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1705	Turraeanthus africanus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC10039 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	268
0.1-0.2	1788
0.2-0.3	5149
0.3-0.4	11243
0.4-0.5	10860
0.5-0.6	6333
0.6-0.7	3937
0.7-0.8	1935
0.8-0.85	485
0.85-0.9	275
0.9-0.95	191
0.95-1	233

Similarity Score	Similarity Level	Natural Product ID

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 NPC10039 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	2108
0.2-0.3	3833
0.3-0.4	1919
0.4-0.5	614
0.5-0.6	268
0.6-0.7	126
0.7-0.8	31
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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