NPASS Compound

Natural Product: NPC201229

Natural Product ID	NPC201229
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DNVPQKQSNYMLRS-PMUSRJBTSA-N
IUPAC Name	n.a.
Synonyms
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: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 73 76 0 0 0 0 0 0 0 0999 V2000 6.8980 -0.2032 1.1940 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9869 -0.5160 -0.2899 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0850 -1.9876 -0.5521 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7959 0.0812 -0.9627 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7282 -0.1364 -2.4399 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5069 -0.4186 -0.3540 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7221 0.3935 0.3187 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4148 -0.0408 0.9564 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3485 -1.5160 0.8851 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3414 0.7567 0.3428 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2218 0.5967 -1.1473 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1606 -0.4342 -1.3236 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5664 -0.5645 -0.0114 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0621 -0.5378 -0.2283 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5963 -1.5782 -0.8285 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0230 -1.5862 -1.0628 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8016 -0.5970 -0.7117 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2600 -0.7561 -1.0147 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1100 -0.0256 -0.0169 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3273 0.1803 1.2385 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1822 1.1037 1.0051 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2551 0.6254 -0.1142 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4319 1.7036 -1.2303 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8609 0.5665 0.2714 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0684 1.8358 -0.0798 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7945 1.8618 0.6649 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0571 0.5595 0.8127 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0696 0.1592 2.2758 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2289 -0.7974 0.2889 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1254 -0.8100 1.7097 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8798 -0.3607 1.6934 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6520 0.8729 1.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8848 0.0377 -0.6618 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4151 -2.5164 0.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0940 -2.4103 -0.8372 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7548 -2.1386 -1.4189 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8449 1.1918 -0.7916 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5402 -0.7949 -2.7878 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7634 -0.6353 -2.7469 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7200 0.8335 -3.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2355 -1.4599 -0.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0566 1.4346 0.4060 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5961 0.2126 2.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3580 -1.8784 1.2683 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6535 -1.9706 1.6494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2551 -1.9705 -0.0979 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5912 1.8483 0.5312 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9048 1.5716 -1.5695 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1816 0.3430 -1.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5769 -1.3936 -1.6920 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5059 -0.0832 -2.1408 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3809 -1.5136 0.5215 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9952 -2.4276 -1.1510 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4613 -2.4646 -1.5567 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4694 -0.3477 -2.0214 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5621 -1.8189 -1.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4521 0.9669 -0.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0398 -0.7671 1.7383 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0082 0.6941 1.9655 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5696 2.0932 0.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5673 1.2253 1.9117 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7674 1.5174 -2.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4125 2.7044 -0.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4742 1.5290 -1.6003 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8167 0.4687 1.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6917 2.6862 0.2694 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9797 1.8797 -1.1718 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9914 2.2871 1.6857 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1380 2.6419 0.1822 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9145 0.7168 2.7919 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8215 0.4891 2.8398 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3387 -0.9010 2.3988 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8835 -0.3114 0.8496 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 8 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 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 19 29 1 0 27 10 1 0 27 13 1 0 24 14 1 0 22 17 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 4 37 1 6 5 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 7 42 1 0 8 43 1 1 9 44 1 0 9 45 1 0 9 46 1 0 10 47 1 6 11 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 1 15 53 1 0 16 54 1 0 18 55 1 0 18 56 1 0 19 57 1 6 20 58 1 0 20 59 1 0 21 60 1 0 21 61 1 0 23 62 1 0 23 63 1 0 23 64 1 0 24 65 1 1 25 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 M END

Standard InCHIKey	DNVPQKQSNYMLRS-PMUSRJBTSA-N
Standard InCHI	InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20-,22-,24+,25+,26+,27+,28+/m0/s1
SMILES	CC(C)[C@@H](C)/C=C/[C@H](C)[C@H]1CC[C@@H]2C3=CC=C4C[C@H](CC[C@@]4(C)[C@@H]3CC[C@]12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	396.34	Volume:	459.499 ? Van der Waals volume.
Dense:	0.863	LogP:	4.919 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.079 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.966 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	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:	0.493	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.631	Fsp³:	0.786
MCE-18:	68.04 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.977	Fluc inhibitor:	0.132 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.605	Promiscuous compounds:	0.164

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.138	MDCK Permeability:	-4.796
Pgp-inhibitor:	0.909	Pgp-substrate:	0.014
PAMPA:	0.032 ? 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%):	0.951	30% Bioavailability (F30%):	0.979
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.137
Plasma Protein Binding (PPB):	98.637%	Volume Distribution (VD):	-0.015
Fu:	0.892% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.474
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.898	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.945
HLM stability:	0.272 ? 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):

11.0

Half-life (T1/2):

0.27

ADMET: Toxicity

hERG Blockers:	0.185	hERG Blockers (10um):	0.345
Human Hepatotoxicity (H-HT):	0.775	Drug-induced Liver Injury (DILI):	0.421
AMES Toxicity:	0.218	Rat Oral Acute Toxicity:	0.394
Maximum Recommended Daily Dose:	0.85	Skin Sensitization:	0.92
Carcinogencity:	0.828	Eye Corrosion:	0.001
Eye Irritation:	0.548	Respiratory Toxicity:	0.861
Drug-induced Neurotoxicity:	0.192	Ototoxicity:	0.833
Hematotoxicity:	0.633	Drug-induced Nephrotoxicity:	0.854
Genotoxicity:	0.51	RPMI-8226 Immunitoxicity:	0.245
A549 Cytotoxicity:	0.712	Hek293 Cytotoxicity:	0.595
BCF:	2.862 ? 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:	4.424 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.267 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.161 ? 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
NPO19825	Litsea japonica	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[14575444]
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16309317]
NPO7688	Artemisia selengensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO15450	Minuria leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9799	Hebeloma longicaudum	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19234	Hymenopappus newberryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19565	Crocus chrysanthus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19364	Aconitum chasmanthum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19364	Aconitum chasmanthum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19364	Aconitum chasmanthum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17577	Azalea ovata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15450	Minuria leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19825	Litsea japonica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7688	Artemisia selengensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19364	Aconitum chasmanthum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18518	Haematomma nemetzii	Species	Haematommataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18499	Podium complanatum	Species	Sphecidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11060	Doris luteorosea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9799	Hebeloma longicaudum	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19234	Hymenopappus newberryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19298	Gerbera crocea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17341	Gambeya africana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17887	Penstemon centranthifolius	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19696	Othonna quercifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18023	Vitex quinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21360	Cordia corymbosa	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19869	Fusicolla aquaeductuum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19565	Crocus chrysanthus	Species	Iridaceae	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 NPC201229 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	23177
0.1-0.2	24037
0.2-0.3	2379
0.3-0.4	179
0.4-0.5	64
0.5-0.6	18
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	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC307965
1.0	High Similarity	NPC18603
1.0	High Similarity	NPC491013
0.7115	Intermediate Similarity	NPC183927
0.5789	Remote Similarity	NPC204188
0.5789	Remote Similarity	NPC80561
0.5789	Remote Similarity	NPC329596
0.5758	Remote Similarity	NPC267510
0.5714	Remote Similarity	NPC134330
0.5614	Remote Similarity	NPC611620
0.5345	Remote Similarity	NPC154330
0.5333	Remote Similarity	NPC49422
0.5333	Remote Similarity	NPC9161
0.5312	Remote Similarity	NPC472220
0.5312	Remote Similarity	NPC97884
0.5254	Remote Similarity	NPC129165
0.5254	Remote Similarity	NPC113733
0.5246	Remote Similarity	NPC291484
0.5167	Remote Similarity	NPC234193
0.5079	Remote Similarity	NPC118648
0.5079	Remote Similarity	NPC475022
0.5079	Remote Similarity	NPC600021

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC201229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7577
0.1-0.2	1413
0.2-0.3	131
0.3-0.4	17
0.4-0.5	6
0.5-0.6	5
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
0.5614	Remote Similarity	NPD7150	Approved
0.5614	Remote Similarity	NPD7151	Phase 4
0.5614	Remote Similarity	NPD7152	Approved
0.5333	Remote Similarity	NPD7143	Approved
0.5333	Remote Similarity	NPD7144	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