NPASS Compound

Natural Product: NPC285761

Natural Product ID	NPC285761
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(20S)-Dammar-24-Ene-3Beta,20-Diol
IUPAC Name	(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms	dammarenediol-II
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL478945
PubChem CID	10895555
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 6.9647 2.7083 0.5231 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6269 1.4651 -0.2562 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5517 1.4231 -1.0271 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2257 0.2146 -1.7831 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9074 -0.4387 -1.5198 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6674 -0.9622 -0.1481 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3046 -1.6584 -0.0459 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1633 -2.1791 1.3720 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9251 -1.5276 1.9495 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1056 -1.3537 0.7289 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1564 -0.7822 -0.2445 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4968 -0.7500 -1.5987 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5164 0.4032 -1.4420 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5713 -0.1411 -0.5126 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0428 -0.4028 0.8468 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6242 0.7988 1.6397 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1171 -1.0830 1.7126 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2342 -0.0288 1.8146 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8171 0.0308 0.4093 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8750 0.6108 -0.5960 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7432 2.0841 -0.6177 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4725 0.2277 -1.9670 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8849 0.7274 -2.1089 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7892 0.3727 -0.9881 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2107 0.5413 0.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4342 1.9170 0.8855 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0262 -0.3976 1.2946 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9358 1.1615 -1.0610 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2466 -2.7371 0.2550 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6030 -1.9922 0.0725 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8530 0.0626 0.9176 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5539 0.3070 -0.1123 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3701 2.4318 1.5227 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7253 3.3119 0.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0339 3.2865 0.7195 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9221 2.3000 -1.1006 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2091 0.5402 -2.8779 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0659 -0.5273 -1.6835 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1485 0.4005 -1.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7571 -1.2230 -2.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3887 -2.5027 -0.7741 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0355 -3.3010 1.3363 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0071 -2.0028 2.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4296 -2.3551 2.5553 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0842 -0.6536 2.5602 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4310 0.2536 -0.0048 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0951 -1.6544 -1.8363 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1744 -0.5182 -2.3919 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0737 1.2368 -0.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9028 0.7018 -2.4153 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8063 -1.1611 -0.9475 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4623 1.0276 1.5933 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1395 1.7329 1.4006 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8063 0.6513 2.7491 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5665 -1.9392 1.2176 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6971 -1.3206 2.6925 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9979 -0.4752 2.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8585 0.9375 2.1535 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9148 -1.0620 0.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0265 2.6381 0.2651 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6645 2.3244 -0.8566 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2935 2.5825 -1.4718 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5190 -0.8879 -1.9589 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8948 0.6310 -2.7979 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2864 0.2081 -3.0305 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9676 1.7982 -2.3264 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1268 -0.6986 -1.1060 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5081 1.9691 1.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4111 2.7044 0.0754 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8379 2.1994 1.7675 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0179 0.0479 2.3186 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0688 -0.3568 0.9459 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5904 -1.4071 1.2904 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6520 0.6757 -1.5343 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2610 -2.8928 -0.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4396 -3.1193 -0.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1128 -3.5113 1.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4881 -2.6253 -0.6858 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1666 -0.0952 1.7801 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7841 1.1227 0.5670 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8669 -0.0529 1.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0653 0.1068 -1.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3304 0.4990 0.6506 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -0.5985 0.2497 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 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 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 24 28 1 0 10 29 1 6 6 30 1 1 6 31 1 0 2 32 1 0 11 7 1 0 20 14 1 0 15 10 1 0 25 19 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 7 41 1 6 8 42 1 0 8 43 1 0 9 44 1 0 9 45 1 0 11 46 1 1 12 47 1 0 12 48 1 0 13 49 1 0 13 50 1 0 14 51 1 6 16 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 6 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 24 67 1 6 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 31 79 1 0 31 80 1 0 31 81 1 0 32 82 1 0 32 83 1 0 32 84 1 0 M END

Standard InCHIKey	NLHQJXWYMZLQJY-TXNIMPHESA-N
Standard InCHI	InChI=1S/C30H52O2/c1-20(2)10-9-16-30(8,32)22-13-18-28(6)21(22)11-12-24-27(5)17-15-25(31)26(3,4)23(27)14-19-29(24,28)7/h10,21-25,31-32H,9,11-19H2,1-8H3/t21-,22+,23+,24-,25+,27+,28-,29-,30+/m1/s1
SMILES	CC(=CCC[C@@]([C@H]1CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)(O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	444.4	Volume:	508.154 ? Van der Waals volume.
Dense:	0.875	LogP:	5.67 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.72 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.409 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	21.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.44	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.675	Fsp³:	0.933
MCE-18:	85.345 ? 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:	0.8	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.743	Promiscuous compounds:	0.277

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.035	MDCK Permeability:	-4.958
Pgp-inhibitor:	0.43	Pgp-substrate:	0.23
PAMPA:	0.773 ? 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):	0.003
20% Bioavailability (F20%):	0.732	30% Bioavailability (F30%):	0.128
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.86	MRP1:	0.98
Plasma Protein Binding (PPB):	97.335%	Volume Distribution (VD):	-0.227
Fu:	4.046% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.221
BSEP inhibitor:	0.954

ADMET: Metabolism

CYP1A2-inhibitor:	0.006	CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.909	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.537 ? 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):

12.312

Half-life (T1/2):

0.399

ADMET: Toxicity

hERG Blockers:	0.135	hERG Blockers (10um):	0.365
Human Hepatotoxicity (H-HT):	0.672	Drug-induced Liver Injury (DILI):	0.061
AMES Toxicity:	0.334	Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.555	Skin Sensitization:	0.989
Carcinogencity:	0.777	Eye Corrosion:	0.278
Eye Irritation:	0.814	Respiratory Toxicity:	0.904
Drug-induced Neurotoxicity:	0.201	Ototoxicity:	0.476
Hematotoxicity:	0.278	Drug-induced Nephrotoxicity:	0.701
Genotoxicity:	0.245	RPMI-8226 Immunitoxicity:	0.067
A549 Cytotoxicity:	0.534	Hek293 Cytotoxicity:	0.327
BCF:	2.376 ? 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:	4.396 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.418 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.114 ? 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
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11411539]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21087017]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21087017]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158164]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	inflorescence	n.a.	PMID[8158164]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1348	Ligustrum japonicus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18340	Ligustrum lucidum	Species	Oleaceae	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	2

Activity Type	# Activity
Organism	2

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
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	7.0	ug.mL-1	PMID[2828553]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	IC50	=	7.0	ug.mL-1	PMID[2828553]

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 NPC285761 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	24230
0.1-0.2	20989
0.2-0.3	3983
0.3-0.4	490
0.4-0.5	112
0.5-0.6	37
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC34930
0.8077	Intermediate Similarity	NPC13554
0.75	Intermediate Similarity	NPC245869
0.7222	Intermediate Similarity	NPC80530
0.7222	Intermediate Similarity	NPC273410
0.6727	Remote Similarity	NPC488511
0.6491	Remote Similarity	NPC215843
0.6429	Remote Similarity	NPC237460
0.6333	Remote Similarity	NPC488508
0.6182	Remote Similarity	NPC606606
0.6	Remote Similarity	NPC480925
0.6	Remote Similarity	NPC48079
0.5968	Remote Similarity	NPC131665
0.5968	Remote Similarity	NPC255387
0.5965	Remote Similarity	NPC600477
0.5965	Remote Similarity	NPC606605
0.5593	Remote Similarity	NPC42853
0.5574	Remote Similarity	NPC126993
0.5556	Remote Similarity	NPC232112
0.55	Remote Similarity	NPC296701
0.55	Remote Similarity	NPC218616
0.5484	Remote Similarity	NPC322313
0.5484	Remote Similarity	NPC102253
0.5484	Remote Similarity	NPC236237
0.5439	Remote Similarity	NPC129829
0.5424	Remote Similarity	NPC91573
0.5345	Remote Similarity	NPC192638
0.5345	Remote Similarity	NPC25511
0.5345	Remote Similarity	NPC600137
0.5333	Remote Similarity	NPC301707
0.5263	Remote Similarity	NPC142712
0.5254	Remote Similarity	NPC66407
0.5254	Remote Similarity	NPC185536
0.5246	Remote Similarity	NPC201725
0.5246	Remote Similarity	NPC3403
0.5211	Remote Similarity	NPC119036
0.5167	Remote Similarity	NPC144075
0.5167	Remote Similarity	NPC301226
0.5161	Remote Similarity	NPC207013
0.5161	Remote Similarity	NPC91387
0.5161	Remote Similarity	NPC231680
0.5161	Remote Similarity	NPC270306
0.5082	Remote Similarity	NPC58631
0.5082	Remote Similarity	NPC248830
0.5082	Remote Similarity	NPC231256
0.5082	Remote Similarity	NPC212241
0.5082	Remote Similarity	NPC178383
0.5079	Remote Similarity	NPC145143
0.5077	Remote Similarity	NPC201406

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC285761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7780
0.1-0.2	1267
0.2-0.3	99
0.3-0.4	2
0.4-0.5	1
0.5-0.6	1
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
0.5484	Remote Similarity	NPD7525	Registered

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