NPASS Compound

Natural Product: NPC248465

Natural Product ID	NPC248465
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FCNPAHAMCOHEQW-QEHLDDBUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	52931354
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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 84 87 0 0 0 0 0 0 0 0999 V2000 -6.7827 0.9980 -2.2201 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7441 0.2738 -1.4212 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7840 0.3445 -0.0653 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8754 1.1514 0.5279 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8178 0.4070 1.3954 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7195 -0.3474 0.7010 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3312 -1.4541 1.5107 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1646 0.6417 1.7170 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6478 -0.8331 -0.2378 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4877 -1.5019 0.4484 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3988 -2.0049 -0.3795 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9466 -3.0354 -1.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3970 -1.2188 -1.0310 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6975 -0.1840 -2.0389 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 0.3647 -2.3468 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6071 -0.2298 -1.3234 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8216 0.5113 -0.9239 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8069 0.4413 -2.0730 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2075 0.6105 -1.6795 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6509 0.5845 -0.4390 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1172 0.7698 -0.1441 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5369 -0.4075 0.7103 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7618 -0.2850 2.0127 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3081 -0.5230 1.7706 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7220 0.3750 0.6934 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4146 1.7433 1.2686 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4828 -0.2957 0.1966 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5454 -0.6255 1.3099 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3406 -1.3844 0.7974 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6409 -0.5152 -0.1894 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1827 0.7752 0.3842 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8949 -0.3248 0.9419 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7486 2.0826 -2.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6775 0.7236 -3.3038 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7752 0.6068 -1.9110 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0122 -0.2632 -1.9854 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4422 1.7123 -0.2592 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3619 1.9939 1.0982 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6840 1.0868 1.6884 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3451 0.0885 2.3401 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2763 -0.4426 0.8784 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3526 -1.6660 1.1388 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4292 -1.2117 2.6000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8031 -2.4385 1.3897 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0479 1.0101 2.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6050 1.4589 1.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5811 0.0438 2.4669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3631 0.0169 -0.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1696 -1.5733 -0.9105 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1788 -0.8045 1.2622 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9138 -2.3721 1.0127 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8007 -2.7138 0.3296 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4034 -2.5323 -2.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5742 -3.7810 -0.9026 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0427 -3.5589 -1.7727 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2449 -1.9796 -1.6140 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3615 0.6295 -1.7745 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0522 -0.6358 -2.9879 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6913 1.4675 -2.2302 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0256 0.1358 -3.3726 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9541 -1.2322 -1.7201 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6984 1.5618 -0.6694 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5187 1.1859 -2.8701 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7313 -0.5518 -2.6003 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9177 0.7702 -2.5106 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2354 1.6883 0.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6671 0.8099 -1.0981 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2540 -1.3470 0.1831 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8982 0.7311 2.4190 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1262 -1.0274 2.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1184 -1.5739 1.4465 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7609 -0.3497 2.7205 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3277 1.9561 1.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8812 2.5651 0.6921 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8505 1.7916 2.2863 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8021 -1.2656 -0.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0929 -1.3507 1.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2785 0.2960 1.8647 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6975 -2.3027 0.3243 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6604 -1.5502 1.6570 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8819 1.0296 0.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7710 1.6380 -0.0138 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3544 0.8223 1.5014 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3581 -0.2631 0.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 3 6 1 0 6 7 1 0 6 8 1 0 6 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 1 22 32 1 0 30 13 1 0 30 16 1 0 27 17 1 0 25 20 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 5 41 1 0 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 10 50 1 0 10 51 1 0 11 52 1 1 12 53 1 0 12 54 1 0 12 55 1 0 13 56 1 6 14 57 1 0 14 58 1 0 15 59 1 0 15 60 1 0 16 61 1 6 17 62 1 1 18 63 1 0 18 64 1 0 19 65 1 0 21 66 1 0 21 67 1 0 22 68 1 6 23 69 1 0 23 70 1 0 24 71 1 0 24 72 1 0 26 73 1 0 26 74 1 0 26 75 1 0 27 76 1 6 28 77 1 0 28 78 1 0 29 79 1 0 29 80 1 0 31 81 1 0 31 82 1 0 31 83 1 0 32 84 1 0 M END

Standard InCHIKey	FCNPAHAMCOHEQW-QEHLDDBUSA-N
Standard InCHI	InChI=1S/C31H52O/c1-8-22(9-2)29(4,5)17-14-21(3)26-12-13-27-25-11-10-23-20-24(32)15-18-30(23,6)28(25)16-19-31(26,27)7/h8,10,21,24-28,32H,9,11-20H2,1-7H3/b22-8+/t21-,24+,25+,26-,27+,28+,30+,31-/m1/s1
SMILES	C/C=C(CC)/C(C)(C)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

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.4	Volume:	514.023 ? Van der Waals volume.
Dense:	0.857	LogP:	8.42 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.44 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.913 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	21.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.409	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.702	Fsp³:	0.871
MCE-18:	73.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.987	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.719	Promiscuous compounds:	0.078

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.109	MDCK Permeability:	-5.043
Pgp-inhibitor:	0.022	Pgp-substrate:	0.055
PAMPA:	0.003 ? 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%):	0.005	30% Bioavailability (F30%):	0.177
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132	MRP1:	0.088
Plasma Protein Binding (PPB):	87.112%	Volume Distribution (VD):	-0.039
Fu:	13.574% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.839
BSEP inhibitor:	0.155

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.356
CYP2D6-inhibitor:	0.009	CYP2D6-substrate:	0.427
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.737 ? 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):

11.329

Half-life (T1/2):

0.513

ADMET: Toxicity

hERG Blockers:	0.159	hERG Blockers (10um):	0.408
Human Hepatotoxicity (H-HT):	0.47	Drug-induced Liver Injury (DILI):	0.194
AMES Toxicity:	0.106	Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.776	Skin Sensitization:	0.909
Carcinogencity:	0.822	Eye Corrosion:	0.172
Eye Irritation:	0.873	Respiratory Toxicity:	0.851
Drug-induced Neurotoxicity:	0.098	Ototoxicity:	0.433
Hematotoxicity:	0.229	Drug-induced Nephrotoxicity:	0.426
Genotoxicity:	0.029	RPMI-8226 Immunitoxicity:	0.059
A549 Cytotoxicity:	0.403	Hek293 Cytotoxicity:	0.711
BCF:	2.926 ? 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:	4.742 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.434 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.454 ? 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
NPO18343	Lavandula pedunculata	Species	Lamiaceae	Eukaryota	Flowers	Yili, China	n.a.	PMID[24621197]
NPO18343	Lavandula pedunculata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36984777]
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	tubers	n.a.	n.a.	PMID[8254346]
NPO14819	Tanacetum chiliophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25243	Rhamnus saxatilis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18343	Lavandula pedunculata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24179	Gymnosporia arbutifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20386	Enterospermum pruinosum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17128	Coleus scutellarioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21459	Boehmeria platyphylla	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18547	Anzia opuntiella	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21051	Acacia discolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16770	Peltogyne venosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24179	Gymnosporia arbutifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21051	Acacia discolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21459	Boehmeria platyphylla	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16770	Peltogyne venosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18547	Anzia opuntiella	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17128	Coleus scutellarioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14819	Tanacetum chiliophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18343	Lavandula pedunculata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20386	Enterospermum pruinosum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25243	Rhamnus saxatilis	Species	Rhamnaceae	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 NPC248465 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	25025
0.1-0.2	21522
0.2-0.3	2941
0.3-0.4	232
0.4-0.5	72
0.5-0.6	27
0.6-0.7	13
0.7-0.8	2
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC162742
0.8	Intermediate Similarity	NPC304309
0.8	Intermediate Similarity	NPC470228
0.7843	Intermediate Similarity	NPC22105
0.7843	Intermediate Similarity	NPC34019
0.7843	Intermediate Similarity	NPC107059
0.7692	Intermediate Similarity	NPC136188
0.7692	Intermediate Similarity	NPC28657
0.7692	Intermediate Similarity	NPC474216
0.7547	Intermediate Similarity	NPC230301
0.7547	Intermediate Similarity	NPC198968
0.7547	Intermediate Similarity	NPC285893
0.7547	Intermediate Similarity	NPC134847
0.7407	Intermediate Similarity	NPC241290
0.7407	Intermediate Similarity	NPC164840
0.7407	Intermediate Similarity	NPC484739
0.7407	Intermediate Similarity	NPC209944
0.7407	Intermediate Similarity	NPC264245
0.7407	Intermediate Similarity	NPC155986
0.7273	Intermediate Similarity	NPC321381
0.717	Intermediate Similarity	NPC600590
0.7143	Intermediate Similarity	NPC472265
0.7143	Intermediate Similarity	NPC59453
0.7037	Intermediate Similarity	NPC154330
0.7018	Intermediate Similarity	NPC603646
0.6897	Remote Similarity	NPC473943
0.678	Remote Similarity	NPC47761
0.678	Remote Similarity	NPC488870
0.661	Remote Similarity	NPC155011
0.6607	Remote Similarity	NPC113733
0.6545	Remote Similarity	NPC221758
0.6491	Remote Similarity	NPC51014
0.6379	Remote Similarity	NPC328714
0.6333	Remote Similarity	NPC240650
0.6271	Remote Similarity	NPC33913
0.6066	Remote Similarity	NPC243985
0.6066	Remote Similarity	NPC280710
0.6	Remote Similarity	NPC318495
0.5968	Remote Similarity	NPC474164
0.5926	Remote Similarity	NPC96319
0.5902	Remote Similarity	NPC477522
0.5862	Remote Similarity	NPC328313
0.5833	Remote Similarity	NPC87604
0.5692	Remote Similarity	NPC601043
0.5692	Remote Similarity	NPC605412
0.5517	Remote Similarity	NPC81306
0.5484	Remote Similarity	NPC1272
0.5484	Remote Similarity	NPC470614
0.5424	Remote Similarity	NPC151519
0.5333	Remote Similarity	NPC109546
0.5333	Remote Similarity	NPC20688
0.5333	Remote Similarity	NPC47982
0.5246	Remote Similarity	NPC76879
0.5246	Remote Similarity	NPC84694
0.5246	Remote Similarity	NPC28862
0.5246	Remote Similarity	NPC143182
0.5161	Remote Similarity	NPC317927
0.5156	Remote Similarity	NPC474752
0.5156	Remote Similarity	NPC474683
0.5147	Remote Similarity	NPC5985
0.5082	Remote Similarity	NPC189972
0.5082	Remote Similarity	NPC317458
0.5079	Remote Similarity	NPC31564
0.5079	Remote Similarity	NPC145879
0.5077	Remote Similarity	NPC475789

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC248465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7791
0.1-0.2	1212
0.2-0.3	116
0.3-0.4	24
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
0.7-0.8	2
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
0.7692	Intermediate Similarity	NPD6942	Phase 4
0.7547	Intermediate Similarity	NPD7339	Approved
0.6545	Remote Similarity	NPD4786	Phase 1
0.5926	Remote Similarity	NPD3701	Pre-clinical
0.5424	Remote Similarity	NPD3667	Phase 4

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