NPASS Compound

Natural Product: NPC485701

Natural Product ID	NPC485701
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XUTWSWVTCRFNFW-YDNPDWLLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101293636
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

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 93 98 0 0 0 0 0 0 0 0999 V2000 11.9210 0.7363 1.4293 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8627 -0.2329 0.9299 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2419 -0.9707 2.0764 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1919 -1.9396 1.6366 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0655 -1.2541 0.9075 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0399 -2.3034 0.4963 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9413 -1.5507 -0.2264 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8353 -2.4538 -0.7062 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1726 -3.1889 0.4388 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5579 -2.2546 1.4503 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5197 -1.3985 0.8237 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2563 -1.3972 1.2102 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2600 -0.5365 0.5657 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9966 -0.4915 0.9019 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9810 0.4128 0.2055 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1750 1.5762 0.9464 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8533 2.3589 0.0235 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2911 1.7738 -0.0111 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9228 1.8957 1.3274 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2205 1.5725 1.5890 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9360 2.2212 2.7874 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4281 1.2292 3.6494 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1224 0.7997 0.7439 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6756 0.3487 -0.5829 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3950 -0.4273 -0.4447 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5124 -1.5498 -1.3821 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7810 -1.6898 -1.7493 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3015 -2.7186 -2.6914 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6011 -0.6898 -1.0926 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8339 -0.6947 -0.9760 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1560 0.3995 -0.5686 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8025 0.5171 -2.0360 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9018 -0.5864 -2.5267 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1119 1.8253 -2.3598 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1343 2.0970 -1.2355 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1952 3.1535 -1.5952 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9242 4.1705 -0.8262 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4377 3.0951 -2.9211 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.8779 -0.9858 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1423 -0.3336 0.0496 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6390 1.3329 -1.5577 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3193 1.5390 0.5887 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1060 0.7654 2.1503 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9495 0.3595 1.2172 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8212 1.7120 0.8965 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7907 0.8807 2.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1090 0.3471 0.3583 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3639 -0.9345 0.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0585 -1.5056 2.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8291 -0.2151 2.8003 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6769 -2.6852 0.9765 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7752 -2.4921 2.4991 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5995 -0.4806 1.5196 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4683 -0.7905 -0.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5047 -2.9966 -0.2408 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6331 -2.8396 1.3578 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4112 -1.0260 -1.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5298 -0.7439 0.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2428 -3.1938 -1.3979 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1141 -1.8249 -1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3774 -3.8442 0.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8947 -3.8297 0.9822 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3700 -1.6533 1.9092 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0349 -2.8897 2.1954 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7602 -0.7185 -0.0016 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9916 -2.0630 2.0261 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5926 0.0995 -0.2384 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3484 -1.1189 1.7023 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9531 3.4233 0.3144 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7856 2.4590 -0.7644 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4538 2.7285 1.9424 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7849 2.7986 2.3267 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2343 2.8736 3.3058 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3377 1.4792 3.9662 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4539 -0.1164 1.3197 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4252 -0.9020 0.5847 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7170 -2.1756 -1.7252 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8684 -3.7043 -2.3559 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3953 -2.8215 -2.6172 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9242 -2.5530 -3.7090 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7312 0.4870 -2.6622 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3591 -1.1679 -3.3799 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9622 -0.1695 -3.0024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5341 -1.2269 -1.7149 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5012 1.6837 -3.2888 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7626 2.6801 -2.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3279 4.3828 0.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1995 4.9211 -1.1864 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5969 3.4859 -2.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4281 2.0659 -3.3117 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9336 3.8301 -3.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5060 1.4905 -1.9923 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0587 2.4587 0.3321 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 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 21 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 27 29 1 0 29 30 2 0 25 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 35 36 1 6 36 37 2 0 36 38 1 0 35 39 1 0 31 40 1 1 24 41 1 6 23 42 1 0 20 43 1 0 39 15 1 0 40 15 1 0 35 17 1 0 31 18 1 0 43 19 1 0 29 24 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 10 64 1 0 11 65 1 0 12 66 1 0 13 67 1 0 14 68 1 0 17 69 1 1 18 70 1 6 19 71 1 1 21 72 1 0 21 73 1 0 22 74 1 0 23 75 1 1 25 76 1 1 26 77 1 0 28 78 1 0 28 79 1 0 28 80 1 0 32 81 1 6 33 82 1 0 33 83 1 0 33 84 1 0 34 85 1 0 34 86 1 0 37 87 1 0 37 88 1 0 38 89 1 0 38 90 1 0 38 91 1 0 41 92 1 0 42 93 1 0 M END

Standard InCHIKey	XUTWSWVTCRFNFW-YDNPDWLLSA-N
Standard InCHI	InChI=1S/C35H50O8/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-33-41-28-26-29-32(21-36,40-29)30(38)34(39)25(19-23(4)27(34)37)35(26,43-33)24(5)20-31(28,42-33)22(2)3/h15-19,24-26,28-30,36,38-39H,2,6-14,20-21H2,1,3-5H3/b16-15+,18-17+/t24-,25-,26-,28-,29+,30-,31-,32+,33?,34-,35+/m1/s1
SMILES	CCCCCCCCCC/C=C/C=C/C12O[C@@H]3[C@@H]4[C@H]5[C@@](CO)([C@H]([C@]6([C@@H](C=C(C)C6=O)[C@]4([C@H](C)C[C@]3(C(=C)C)O1)O2)O)O)O5

Calculated Properties

Physi-Chem Properties

Molecular Weight:	598.35	Volume:	619.717 ? Van der Waals volume.
Dense:	0.966	LogP:	5.298 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.282 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.986 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	28.0
TPSA:	117.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.12	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.635	Fsp³:	0.743
MCE-18:	100.525 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.582	Fluc inhibitor:	0.095 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.017 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.166	Promiscuous compounds:	0.165

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.139	MDCK Permeability:	-4.711
Pgp-inhibitor:	0.001	Pgp-substrate:	0.009
PAMPA:	0.016 ? 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):	0.02
20% Bioavailability (F20%):	0.94	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.986
Plasma Protein Binding (PPB):	97.926%	Volume Distribution (VD):	0.234
Fu:	1.579% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.048
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.994
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.202
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.907	CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.327 ? 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):

5.364

Half-life (T1/2):

0.802

ADMET: Toxicity

hERG Blockers:	0.092	hERG Blockers (10um):	0.387
Human Hepatotoxicity (H-HT):	0.341	Drug-induced Liver Injury (DILI):	0.245
AMES Toxicity:	0.96	Rat Oral Acute Toxicity:	0.493
Maximum Recommended Daily Dose:	0.141	Skin Sensitization:	1.0
Carcinogencity:	0.539	Eye Corrosion:	0.003
Eye Irritation:	0.665	Respiratory Toxicity:	0.504
Drug-induced Neurotoxicity:	0.424	Ototoxicity:	0.717
Hematotoxicity:	0.668	Drug-induced Nephrotoxicity:	0.4
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.251
A549 Cytotoxicity:	0.937	Hek293 Cytotoxicity:	0.904
BCF:	2.232 ? 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:	5.551 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.645 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.43 ? 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
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34770847]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	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

Activity Type	# Activity
EC50	1
CC50	1
Ratio CC50/EC50	1

Activity Type	# Activity
Cell line	1
Organism	1
Others	1

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
NPT25	Cell line	MT4	Homo sapiens	CC50	>=	16700.0	nM	PMID[26562066]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	13.0	nM	PMID[26562066]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	>=	1284.0	n.a.	PMID[26562066]

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 NPC485701 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	17660
0.1-0.2	30580
0.2-0.3	1493
0.3-0.4	46
0.4-0.5	27
0.5-0.6	7
0.6-0.7	16
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474508
1.0	High Similarity	NPC473485
1.0	High Similarity	NPC171411
0.9853	High Similarity	NPC251564
0.9853	High Similarity	NPC477189
0.9	High Similarity	NPC162495
0.7821	Intermediate Similarity	NPC182266
0.7821	Intermediate Similarity	NPC475154
0.7821	Intermediate Similarity	NPC485700
0.7792	Intermediate Similarity	NPC485693
0.7692	Intermediate Similarity	NPC223356
0.7692	Intermediate Similarity	NPC298697
0.7692	Intermediate Similarity	NPC475500
0.7692	Intermediate Similarity	NPC100017
0.7692	Intermediate Similarity	NPC481742
0.7662	Intermediate Similarity	NPC475314
0.7662	Intermediate Similarity	NPC102997
0.7595	Intermediate Similarity	NPC75831
0.7595	Intermediate Similarity	NPC471137
0.75	Intermediate Similarity	NPC471136
0.75	Intermediate Similarity	NPC116727
0.75	Intermediate Similarity	NPC39509
0.7407	Intermediate Similarity	NPC481744
0.7407	Intermediate Similarity	NPC481743
0.7195	Intermediate Similarity	NPC475139
0.7125	Intermediate Similarity	NPC180902
0.7	Intermediate Similarity	NPC324104
0.7	Intermediate Similarity	NPC473548
0.6974	Remote Similarity	NPC475273
0.6974	Remote Similarity	NPC168849
0.6974	Remote Similarity	NPC217901
0.6974	Remote Similarity	NPC611341
0.6962	Remote Similarity	NPC475606
0.6667	Remote Similarity	NPC92598
0.6667	Remote Similarity	NPC43304
0.6667	Remote Similarity	NPC481753
0.6667	Remote Similarity	NPC477188
0.6667	Remote Similarity	NPC477190
0.6556	Remote Similarity	NPC68282
0.6452	Remote Similarity	NPC101786
0.6316	Remote Similarity	NPC481773
0.6087	Remote Similarity	NPC164150
0.6087	Remote Similarity	NPC481754
0.6	Remote Similarity	NPC476091
0.5895	Remote Similarity	NPC130886
0.5895	Remote Similarity	NPC486153
0.5825	Remote Similarity	NPC69240
0.5773	Remote Similarity	NPC481774
0.5333	Remote Similarity	NPC191992
0.5204	Remote Similarity	NPC481745
0.5052	Remote Similarity	NPC475389

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC485701 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6924
0.1-0.2	2197
0.2-0.3	29
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
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
		NPD

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