NPASS Compound

Natural Product: NPC317429

Natural Product ID	NPC317429
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GHGKPLPBPGYSOO-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	286499
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 78 81 0 0 0 0 0 0 0 0999 V2000 5.9865 2.8894 1.1721 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0898 2.1363 -0.0913 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3872 0.7414 -0.0402 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0018 1.0213 0.2769 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8842 0.1136 0.4197 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3469 -0.7152 -0.6563 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3153 -1.7134 -1.2057 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1410 -1.4788 -0.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6863 -2.4136 -1.3570 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7129 -2.8103 -0.7954 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2008 -1.4288 -0.5512 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0738 -0.7697 0.2209 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2427 0.6793 0.0182 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6965 1.0114 -0.4041 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7023 0.1991 0.3667 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5614 -1.2557 0.0009 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5297 -1.7300 -1.0589 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7600 -0.9603 -1.1633 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0367 0.1635 -0.5537 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0493 0.7814 0.3513 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6837 0.7059 1.7491 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0319 1.3497 1.7620 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9468 1.0210 0.6504 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3493 0.8733 -0.7055 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5965 -0.1931 0.9711 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9636 2.2762 0.0661 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2303 -1.0232 1.7370 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1986 -0.1734 0.7676 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3020 0.2225 1.3937 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8961 -1.6267 0.9191 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1423 3.6405 1.0493 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7351 2.3467 2.0802 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9254 3.4769 1.3771 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1232 1.9633 -0.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5606 2.6572 -0.9422 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4873 0.4340 -1.1255 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0336 1.6009 1.2976 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7042 1.9271 -0.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0218 0.7358 0.8654 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0902 -0.5596 1.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0700 -0.0868 -1.5770 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8476 -2.3026 -2.0571 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -1.3353 -1.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5715 -2.5142 -0.4736 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5144 -2.2054 0.5718 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5380 -1.8610 -2.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2484 -3.3344 -1.3926 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5982 -3.3485 0.1566 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2815 -3.3544 -1.5646 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1974 -0.8866 -1.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3709 1.1862 -0.7131 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1515 1.2607 0.9912 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8285 2.1032 -0.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8342 0.9633 -1.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3532 0.2786 1.4555 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7895 -1.8624 0.9019 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8239 -2.8065 -0.8783 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0406 -1.7532 -2.0644 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5431 -1.3656 -1.8253 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0126 1.2952 2.4067 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7057 -0.3193 2.1396 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5333 0.9876 2.7126 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9754 2.4635 1.9356 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7401 1.8264 0.6316 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0369 0.2393 -1.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1506 1.8421 -1.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0117 -0.5285 0.1167 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6404 2.4606 -0.9503 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3848 2.8203 0.8316 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0076 2.6985 0.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1839 -0.0790 2.3148 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6651 -1.6023 2.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0837 -1.6488 1.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6630 1.2165 1.3479 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8696 -0.4815 1.9796 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9642 -1.8266 1.4196 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9034 -2.1171 -0.0953 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7509 -2.1379 1.4714 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 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 20 26 1 0 12 27 1 0 3 28 1 0 28 29 2 0 28 30 1 0 12 8 1 0 16 11 1 0 20 15 1 0 24 19 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 2 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 15 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 21 60 1 0 21 61 1 0 22 62 1 0 22 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	GHGKPLPBPGYSOO-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,20-21,23-27,30H,2,7-9,11-18H2,1,3-6H3
SMILES	CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(=C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.37	Volume:	479.432 ? Van der Waals volume.
Dense:	0.86	LogP:	6.947 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.975 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.165 ? 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:	0.439	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.498	Fsp³:	0.862
MCE-18:	69.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.866	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:	0.01 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.555	Promiscuous compounds:	0.018

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.883	MDCK Permeability:	-4.748
Pgp-inhibitor:	0.016	Pgp-substrate:	0.002
PAMPA:	0.013 ? 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%):	0.001	30% Bioavailability (F30%):	0.035
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999	MRP1:	0.999
Plasma Protein Binding (PPB):	93.415%	Volume Distribution (VD):	0.347
Fu:	10.319% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.68	BCRP inhibitor:	0.144
BSEP inhibitor:	0.619

ADMET: Metabolism

CYP1A2-inhibitor:	0.015	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.871	CYP2C19-substrate:	0.535
CYP2C9-inhibitor:	0.258	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.409	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.971	CYP3A4-substrate:	1.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.986
HLM stability:	0.72 ? 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):

15.307

Half-life (T1/2):

0.56

ADMET: Toxicity

hERG Blockers:	0.317	hERG Blockers (10um):	0.769
Human Hepatotoxicity (H-HT):	0.701	Drug-induced Liver Injury (DILI):	0.082
AMES Toxicity:	0.052	Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.853	Skin Sensitization:	0.324
Carcinogencity:	0.467	Eye Corrosion:	0.005
Eye Irritation:	0.227	Respiratory Toxicity:	0.755
Drug-induced Neurotoxicity:	0.314	Ototoxicity:	0.878
Hematotoxicity:	0.137	Drug-induced Nephrotoxicity:	0.091
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.319	Hek293 Cytotoxicity:	0.413
BCF:	2.57 ? 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:	5.294 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.316 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.599 ? 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
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(00)97029-8]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[18496782]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18603435]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[20469887]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466114]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28737396]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36431782]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Embryo	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18674	Juglans regia	Species	Juglandaceae	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
NPO18674	Juglans regia	Other (raw)	Seed	1.75	0	3.5	mg/100g	Database [DUKE]

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 NPC317429 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	24426
0.1-0.2	21756
0.2-0.3	3297
0.3-0.4	229
0.4-0.5	74
0.5-0.6	27
0.6-0.7	18
0.7-0.8	1
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC285893
0.8542	High Similarity	NPC162742
0.8542	High Similarity	NPC304309
0.8542	High Similarity	NPC470228
0.84	Intermediate Similarity	NPC230301
0.8367	Intermediate Similarity	NPC34019
0.8039	Intermediate Similarity	NPC198968
0.8	Intermediate Similarity	NPC22105
0.8	Intermediate Similarity	NPC107059
0.7843	Intermediate Similarity	NPC136188
0.7843	Intermediate Similarity	NPC28657
0.7843	Intermediate Similarity	NPC474216
0.7692	Intermediate Similarity	NPC134847
0.7547	Intermediate Similarity	NPC241290
0.7547	Intermediate Similarity	NPC164840
0.7547	Intermediate Similarity	NPC484739
0.7547	Intermediate Similarity	NPC209944
0.7547	Intermediate Similarity	NPC155986
0.7407	Intermediate Similarity	NPC321381
0.7273	Intermediate Similarity	NPC59453
0.7222	Intermediate Similarity	NPC264245
0.7143	Intermediate Similarity	NPC603646
0.7037	Intermediate Similarity	NPC113733
0.7018	Intermediate Similarity	NPC473943
0.6981	Remote Similarity	NPC600590
0.6964	Remote Similarity	NPC472265
0.6897	Remote Similarity	NPC488870
0.6852	Remote Similarity	NPC154330
0.6724	Remote Similarity	NPC155011
0.6667	Remote Similarity	NPC221758
0.661	Remote Similarity	NPC47761
0.6607	Remote Similarity	NPC51014
0.6379	Remote Similarity	NPC33913
0.625	Remote Similarity	NPC328313
0.6207	Remote Similarity	NPC328714
0.6167	Remote Similarity	NPC243985
0.6167	Remote Similarity	NPC280710
0.6167	Remote Similarity	NPC240650
0.6102	Remote Similarity	NPC318495
0.6066	Remote Similarity	NPC474164
0.6038	Remote Similarity	NPC96319
0.6	Remote Similarity	NPC477522
0.5932	Remote Similarity	NPC87604
0.5781	Remote Similarity	NPC601043
0.5781	Remote Similarity	NPC605412
0.5738	Remote Similarity	NPC474752
0.5738	Remote Similarity	NPC474683
0.5667	Remote Similarity	NPC145879
0.5614	Remote Similarity	NPC81306
0.5593	Remote Similarity	NPC28862
0.5574	Remote Similarity	NPC1272
0.5574	Remote Similarity	NPC470614
0.5517	Remote Similarity	NPC151519
0.5424	Remote Similarity	NPC20688
0.541	Remote Similarity	NPC31564
0.5333	Remote Similarity	NPC76879
0.5238	Remote Similarity	NPC44083
0.5167	Remote Similarity	NPC109546
0.5167	Remote Similarity	NPC247325
0.5167	Remote Similarity	NPC317458
0.5167	Remote Similarity	NPC47982
0.5161	Remote Similarity	NPC26959
0.5156	Remote Similarity	NPC268406
0.5152	Remote Similarity	NPC474349
0.5152	Remote Similarity	NPC474189
0.5082	Remote Similarity	NPC84694
0.5082	Remote Similarity	NPC143182
0.5082	Remote Similarity	NPC20610
0.5075	Remote Similarity	NPC176012

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC317429 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7766
0.1-0.2	1223
0.2-0.3	126
0.3-0.4	28
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD7339	Approved
0.7843	Intermediate Similarity	NPD6942	Phase 4
0.6667	Remote Similarity	NPD4786	Phase 1
0.6038	Remote Similarity	NPD3701	Pre-clinical
0.5517	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