NPASS Compound

Natural Product: NPC471940

Natural Product ID	NPC471940
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CEEFNBYRKPOUJV-GBSKIJSSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3309439
PubChem CID	n.a.
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 96 99 0 0 0 0 0 0 0 0999 V2000 10.5962 -3.1090 -0.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4493 -1.9648 0.8954 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0472 -1.3384 0.6053 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0779 -2.4227 0.8550 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6634 -2.1058 0.7589 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0080 -1.6434 -0.4713 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4014 -0.3329 -1.0476 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4834 0.0168 -2.2387 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1092 0.2722 -1.8039 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6766 0.3104 -0.5684 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2782 0.5714 -0.2935 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.6098 0.9563 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 0.8724 1.2269 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0988 0.8881 2.4597 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5261 1.0980 0.2846 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9060 1.3728 0.5296 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6257 0.0334 0.1413 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9056 -0.5970 -1.0067 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3860 -0.3176 -2.3200 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3969 -1.6712 -1.6929 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4269 -2.5541 -2.4951 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4266 -3.8069 -1.9290 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7655 -2.2138 -1.6128 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2424 -2.2731 -0.2277 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9197 -0.9525 0.0822 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0826 0.2228 -0.0810 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1935 0.6149 -1.4502 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5084 1.4474 0.6868 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9021 2.7028 0.0420 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4055 2.4998 -0.2565 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2293 2.3314 -1.6462 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7291 3.7600 0.0543 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0390 3.9720 1.1296 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9038 4.9295 -0.8838 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9701 3.6858 1.0560 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6346 4.8823 0.9425 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2335 5.1571 -0.1144 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6276 5.8239 2.0778 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9947 1.5870 0.7559 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5820 -1.2487 1.3346 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9106 -2.5331 1.3131 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4586 -3.1179 0.0235 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9790 -4.0344 -0.6074 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6278 -3.3131 2.3839 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3191 -2.6879 0.7070 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8645 -3.5115 -2.1704 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2318 -4.0396 0.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6665 -3.3126 -0.3363 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0160 -2.9526 -1.0081 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4957 -2.3356 1.9195 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2433 -1.2325 0.7043 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9859 -0.4617 1.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0971 -1.0079 -0.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3466 -3.3084 0.1643 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2585 -2.8390 1.9063 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4847 -1.2708 1.5598 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0169 -2.9349 1.2437 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8945 -1.8174 -0.3990 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2545 -2.4194 -1.3200 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2879 0.4843 -0.2976 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4331 -0.2620 -1.4236 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9306 0.9442 -2.6833 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5868 -0.7788 -3.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3838 0.4479 -2.6341 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3531 0.1871 0.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6100 0.7327 -1.1262 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5692 0.4387 1.7202 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0302 1.5177 1.6079 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4520 -0.5829 1.0475 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8074 -0.4281 -0.9569 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8027 -2.5926 -3.5493 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4170 -2.0964 -2.4620 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2952 -4.4767 -2.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5181 -1.6182 -2.2126 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7605 -0.9137 -0.6876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1795 0.6784 -1.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0776 1.3771 1.7050 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4222 2.9669 -0.8767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8565 2.9296 -2.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5290 4.9119 1.3653 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9510 3.2203 1.8898 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8555 4.8653 -1.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1059 4.8926 -1.6831 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7479 5.8757 -0.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4670 5.6177 2.7901 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6340 6.8950 1.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6918 5.7097 2.7005 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5504 0.7557 0.2788 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3383 1.7176 1.8225 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3611 2.5269 0.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8123 -0.6017 2.1942 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4510 -2.7137 2.8074 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9482 -3.5818 3.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0839 -4.2024 1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7441 -2.6547 1.6003 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6936 -4.1697 -1.4296 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 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 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 6 21 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 6 30 32 1 0 32 33 2 0 32 34 1 0 29 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 28 39 1 0 25 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 41 44 1 0 24 45 1 1 23 46 1 0 30 16 1 0 26 17 1 0 20 18 1 0 42 24 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 2 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 6 58 1 0 6 59 1 0 7 60 1 0 7 61 1 0 8 62 1 0 8 63 1 0 9 64 1 0 10 65 1 0 11 66 1 0 12 67 1 0 16 68 1 1 17 69 1 1 18 70 1 6 21 71 1 0 21 72 1 0 22 73 1 0 23 74 1 6 25 75 1 6 27 76 1 0 28 77 1 1 29 78 1 6 31 79 1 0 33 80 1 0 33 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 38 85 1 0 38 86 1 0 38 87 1 0 39 88 1 0 39 89 1 0 39 90 1 0 40 91 1 0 44 92 1 0 44 93 1 0 44 94 1 0 45 95 1 0 46 96 1 0 M END

Standard InCHIKey	CEEFNBYRKPOUJV-GBSKIJSSSA-N
Standard InCHI	InChI=1S/C35H50O11/c1-7-8-9-10-11-12-13-14-15-16-17-25(38)45-30-26-29-32(19-36,46-29)31(40)35(43)24(18-21(4)27(35)39)34(26,42)22(5)28(44-23(6)37)33(30,41)20(2)3/h14-18,22,24,26,28-31,36,40-43H,2,7-13,19H2,1,3-6H3/b15-14+,17-16+/t22-,24+,26+,28-,29+,30-,31-,32+,33+,34+,35-/m1/s1
SMILES	CCCCCCCC/C=C/C=C/C(=O)O[C@@H]1[C@@H]2[C@@H]3O[C@]3(CO)[C@H]([C@]3([C@H]([C@@]2(O)[C@@H]([C@H]([C@@]1(O)C(=C)C)OC(=O)C)C)C=C(C3=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	646.34	Volume:	657.927 ? Van der Waals volume.
Dense:	0.982	LogP:	3.746 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.513 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.781 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	24.0
TPSA:	183.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.049	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.687	Fsp³:	0.686
MCE-18:	85.424 ? 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:	0.403	Fluc inhibitor:	0.073 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.014 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.203	Promiscuous compounds:	0.53

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.225	MDCK Permeability:	-4.882
Pgp-inhibitor:	0.0	Pgp-substrate:	0.185
PAMPA:	0.547 ? 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):	0.772
20% Bioavailability (F20%):	0.989	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.276
Plasma Protein Binding (PPB):	92.12%	Volume Distribution (VD):	-0.235
Fu:	8.189% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.075
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.995
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.162	CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	0.929	CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.484 ? 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):

2.628

Half-life (T1/2):

1.312

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.189
Human Hepatotoxicity (H-HT):	0.505	Drug-induced Liver Injury (DILI):	0.445
AMES Toxicity:	0.767	Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.27	Skin Sensitization:	1.0
Carcinogencity:	0.227	Eye Corrosion:	0.01
Eye Irritation:	0.749	Respiratory Toxicity:	0.544
Drug-induced Neurotoxicity:	0.092	Ototoxicity:	0.787
Hematotoxicity:	0.707	Drug-induced Nephrotoxicity:	0.901
Genotoxicity:	0.058	RPMI-8226 Immunitoxicity:	0.19
A549 Cytotoxicity:	0.891	Hek293 Cytotoxicity:	0.622
BCF:	1.098 ? 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:	4.453 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.97 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.094 ? 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
IC50	1

Activity Type	# Activity
Cell line	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
NPT81	Cell line	A549	Homo sapiens	IC50	=	24.0	nM	PMID[8496705]

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 NPC471940 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	18766
0.1-0.2	28276
0.2-0.3	2636
0.3-0.4	110
0.4-0.5	50
0.5-0.6	8
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC208543
0.9848	High Similarity	NPC167154
0.9848	High Similarity	NPC481752
0.8971	High Similarity	NPC481749
0.8025	Intermediate Similarity	NPC251139
0.7973	Intermediate Similarity	NPC263899
0.7901	Intermediate Similarity	NPC481776
0.72	Intermediate Similarity	NPC473919
0.6711	Remote Similarity	NPC481747
0.642	Remote Similarity	NPC471939
0.6383	Remote Similarity	NPC481775
0.6265	Remote Similarity	NPC236999
0.589	Remote Similarity	NPC481748
0.5802	Remote Similarity	NPC485694
0.5732	Remote Similarity	NPC473802
0.5604	Remote Similarity	NPC481746
0.5517	Remote Similarity	NPC473709
0.5055	Remote Similarity	NPC182266
0.5055	Remote Similarity	NPC475154
0.5055	Remote Similarity	NPC485700

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6787
0.1-0.2	2314
0.2-0.3	49
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