NPASS Compound

Natural Product: NPC164352

Natural Product ID	NPC164352
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NPJICTMALKLTFW-NEOYQNEMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	70699351
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 101105 0 0 0 0 0 0 0 0999 V2000 -6.1251 -1.5558 -2.5529 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5868 -1.9085 -1.1927 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0814 -0.8393 -0.2889 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1353 0.2349 0.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5219 1.0885 -0.9010 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6857 2.2332 -0.4911 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5681 3.2178 0.3501 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4478 2.0931 0.2618 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5421 1.4662 1.6326 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5647 0.2771 1.5502 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4851 0.9838 0.7895 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2961 0.2344 0.3913 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3423 -0.2993 1.6840 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6374 -0.8929 1.3270 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2825 -0.5247 0.2603 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6083 -1.1910 -0.0246 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6180 -0.0432 0.0514 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3111 0.8833 -1.0983 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9642 1.5442 -0.9234 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8622 0.4950 -0.7401 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6109 -0.2425 -2.0250 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6759 1.2374 -0.1950 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0954 2.2256 -1.1279 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3171 2.6168 -0.9549 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2308 1.5323 -0.4080 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4449 0.5326 -1.4754 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8744 -0.5805 -0.0583 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5738 -0.3272 1.1205 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9829 -1.5932 1.8314 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9512 -2.3363 0.9704 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4542 -1.5128 -0.1937 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6659 -0.0740 0.1359 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0509 0.1857 0.7280 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0029 -0.3996 -0.1090 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6844 0.4811 0.9156 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6809 -2.0617 -0.5673 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3021 -3.4490 0.4300 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6635 -1.2132 2.9896 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5662 -1.5676 0.9843 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0799 -0.5383 1.9305 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6085 -2.5531 0.5467 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4664 -2.4137 -3.2324 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0330 -1.5535 -2.7014 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5815 -0.6253 -2.8954 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6709 -2.3759 -0.6786 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2925 -2.7985 -1.1998 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0030 -0.3971 -0.7817 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6059 0.7936 0.9669 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3170 -0.3695 0.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0296 0.4331 -1.6385 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3901 1.5343 -1.4964 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4563 2.8911 -1.3906 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9178 2.7289 1.2586 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8676 4.0274 0.6402 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3419 3.6576 -0.2870 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1236 3.1866 0.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0524 2.1287 2.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5097 1.2412 2.0137 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2374 -0.0180 2.5569 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9794 -0.5862 1.0418 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1806 1.8588 1.4006 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4058 -0.6245 -0.2595 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3568 -1.0262 2.1770 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5434 0.5820 2.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0357 -1.6614 2.0018 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5368 -1.5263 -1.0873 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8327 -1.9943 0.6774 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4581 0.4489 1.0254 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4204 0.3266 -2.0276 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0781 1.6728 -1.0855 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9800 2.2000 -0.0557 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7436 2.1063 -1.8523 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3688 -1.3312 -1.8360 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5724 -0.3008 -2.6241 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7852 0.1338 -2.6383 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0828 1.7931 0.7151 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2799 2.0125 -2.2246 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7009 3.1810 -0.9900 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3694 3.4454 -0.1901 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7013 3.0348 -1.9109 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9204 -0.4210 -1.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4208 0.1754 -1.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8813 0.9613 -2.3777 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9276 0.2460 1.8509 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0846 -2.1673 2.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7979 -2.7311 1.5822 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7791 -1.6335 -1.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6627 0.4884 -0.8426 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2177 1.2786 0.7789 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1590 -0.2955 1.7132 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9094 -0.2753 0.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8161 -1.8165 -1.5313 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9490 -4.2031 0.3449 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8490 -1.9410 3.6032 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6877 -2.0993 1.3939 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2705 -0.1964 2.5995 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8801 -0.9513 2.5901 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5165 0.3665 1.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1844 -3.5871 0.4437 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0984 -2.3126 -0.4083 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4286 -2.5603 1.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 17 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 3 39 1 0 39 40 1 0 39 41 1 0 25 8 1 0 35 28 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 2 46 1 0 3 47 1 6 4 48 1 0 4 49 1 0 5 50 1 0 5 51 1 0 6 52 1 6 7 53 1 0 7 54 1 0 7 55 1 0 8 56 1 1 9 57 1 0 9 58 1 0 10 59 1 0 10 60 1 0 11 61 1 1 12 62 1 6 13 63 1 0 13 64 1 0 14 65 1 0 16 66 1 0 16 67 1 0 17 68 1 1 18 69 1 0 18 70 1 0 19 71 1 0 19 72 1 0 21 73 1 0 21 74 1 0 21 75 1 0 22 76 1 1 23 77 1 0 23 78 1 0 24 79 1 0 24 80 1 0 26 81 1 0 26 82 1 0 26 83 1 0 28 84 1 1 29 85 1 0 30 86 1 0 31 87 1 6 32 88 1 0 33 89 1 0 33 90 1 0 34 91 1 0 36 92 1 0 37 93 1 0 38 94 1 0 39 95 1 0 40 96 1 0 40 97 1 0 40 98 1 0 41 99 1 0 41100 1 0 41101 1 0 M END

Standard InCHIKey	NPJICTMALKLTFW-NEOYQNEMSA-N
Standard InCHI	InChI=1S/C35H60O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h10,20-22,24-33,36-39H,7-9,11-19H2,1-6H3/t21-,22-,24+,25+,26-,27+,28+,29?,30-,31?,32?,33-,34+,35-/m1/s1
SMILES	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1C(C([C@@H](C(CO)O1)O)O)O)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.44	Volume:	621.239 ? Van der Waals volume.
Dense:	0.928	LogP:	5.821 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.233 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.784 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	26.0
TPSA:	99.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.257	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.99	Fsp³:	0.943
MCE-18:	90.588 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.975	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.213	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.562	MDCK Permeability:	-5.164
Pgp-inhibitor:	0.0	Pgp-substrate:	0.134
PAMPA:	0.78 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.012	30% Bioavailability (F30%):	0.69
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009	MRP1:	0.006
Plasma Protein Binding (PPB):	76.162%	Volume Distribution (VD):	-0.415
Fu:	18.991% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.114
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.773 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.245

Half-life (T1/2):

1.073

ADMET: Toxicity

hERG Blockers:	0.277	hERG Blockers (10um):	0.481
Human Hepatotoxicity (H-HT):	0.465	Drug-induced Liver Injury (DILI):	0.262
AMES Toxicity:	0.267	Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.18	Skin Sensitization:	0.982
Carcinogencity:	0.28	Eye Corrosion:	0.001
Eye Irritation:	0.073	Respiratory Toxicity:	0.317
Drug-induced Neurotoxicity:	0.032	Ototoxicity:	0.94
Hematotoxicity:	0.226	Drug-induced Nephrotoxicity:	0.2
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.074
A549 Cytotoxicity:	0.617	Hek293 Cytotoxicity:	0.696
BCF:	2.693 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.61 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.539 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.293 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15621610]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28453270]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21373	Vitex trifolia	Species	Lamiaceae	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	Organism Name	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

Molecular-level activity

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

In vitro activity

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

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC164352 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	18590
0.1-0.2	24403
0.2-0.3	5511
0.3-0.4	1154
0.4-0.5	149
0.5-0.6	30
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC22140
1.0	High Similarity	NPC243728
0.7973	Intermediate Similarity	NPC486114
0.7971	Intermediate Similarity	NPC158088
0.7681	Intermediate Similarity	NPC473890
0.7606	Intermediate Similarity	NPC470434
0.75	Intermediate Similarity	NPC282669
0.726	Intermediate Similarity	NPC608180
0.7215	Intermediate Similarity	NPC295389
0.6585	Remote Similarity	NPC272015
0.6471	Remote Similarity	NPC44083
0.6301	Remote Similarity	NPC207617
0.6301	Remote Similarity	NPC607440
0.622	Remote Similarity	NPC296686
0.6071	Remote Similarity	NPC181845
0.5882	Remote Similarity	NPC230301
0.5696	Remote Similarity	NPC21064
0.5543	Remote Similarity	NPC295980
0.5532	Remote Similarity	NPC470748
0.5529	Remote Similarity	NPC242748
0.55	Remote Similarity	NPC285231
0.5465	Remote Similarity	NPC220048
0.5444	Remote Similarity	NPC86020
0.5443	Remote Similarity	NPC267510
0.5402	Remote Similarity	NPC318135
0.5375	Remote Similarity	NPC154452
0.5375	Remote Similarity	NPC121072
0.5319	Remote Similarity	NPC94272
0.5287	Remote Similarity	NPC251614
0.5217	Remote Similarity	NPC162742
0.5217	Remote Similarity	NPC304309
0.5217	Remote Similarity	NPC470228
0.5211	Remote Similarity	NPC20610
0.5205	Remote Similarity	NPC153987
0.5152	Remote Similarity	NPC477809
0.5102	Remote Similarity	NPC98696
0.5102	Remote Similarity	NPC486388
0.51	Remote Similarity	NPC6806
0.5056	Remote Similarity	NPC165439
0.5052	Remote Similarity	NPC305423
0.5052	Remote Similarity	NPC113044
0.5052	Remote Similarity	NPC283829
0.5052	Remote Similarity	NPC14704
0.5052	Remote Similarity	NPC161676
0.5052	Remote Similarity	NPC600116

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC164352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6843
0.1-0.2	2092
0.2-0.3	189
0.3-0.4	19
0.4-0.5	6
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5882	Remote Similarity	NPD7339	Approved

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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