NPASS Compound

Natural Product: NPC534965

Natural Product ID	NPC534965
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{a}~{R},8~{R},9~{S},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{S})-9-hydroxy-8-(hydroxymethyl)-1-isopropenyl-5~{a},5~{b},8,11~{a}-tetramethyl-1,2,3,4,5,6,7,7~{a},9,10,11,11~{b},12,13,13~{a},13~{b}-hexadecahydrocyclopenta[a]chrysene-3~{a}-carboxylic acid
IUPAC Name	(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{a}~{R},8~{R},9~{S},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{S})-9-hydroxy-8-(hydroxymethyl)-1-isopropenyl-5~{a},5~{b},8,11~{a}-tetramethyl-1,2,3,4,5,6,7,7~{a},9,10,11,11~{b},12,13,13~{a},13~{b}-hexadecahydrocyclopenta[a]chrysene-3~{a}-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 82 86 0 0 0 0 0 0 0 0999 V2000 -3.4815 -0.6611 3.1424 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8640 0.2884 2.3157 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0309 1.6438 2.9057 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1226 0.0053 0.9212 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3198 -1.4525 0.5621 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3599 -1.4273 -0.9453 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9097 -0.0556 -1.3638 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0853 0.6741 -1.9360 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4176 1.7427 -1.3539 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7811 0.2320 -3.0285 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9202 -0.2226 -2.4771 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6453 -0.8455 -2.0562 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -0.3659 -0.7503 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9340 -1.5269 0.1657 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9081 0.7807 -0.1637 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2728 1.3411 1.0584 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1629 1.7943 0.8193 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8992 0.6599 0.2355 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4106 0.7934 0.2446 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9504 1.8252 -0.6576 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7855 1.1671 1.6690 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2290 1.0232 1.9914 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0204 0.0456 1.2372 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9802 0.7494 0.4665 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3139 -0.8765 0.3048 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1180 -1.0465 -0.9941 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4097 -2.2717 0.9486 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8033 -3.2526 0.2116 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8997 -0.6132 0.0162 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5203 -1.0042 -1.3655 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0898 -0.8800 -1.7425 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3147 0.2148 -1.0712 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2144 1.3495 -2.0687 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3567 0.6529 -0.1468 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3100 -1.7004 2.8935 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2993 -0.4437 4.2125 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8834 1.6614 3.6255 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1157 1.8465 3.5242 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1869 2.4209 2.1291 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2110 0.3940 0.7775 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3340 -1.8374 0.8849 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6124 -2.1484 0.9816 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3752 -1.6366 -1.3567 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7075 -2.2208 -1.3287 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7939 0.3554 -3.0272 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4178 -0.9325 -3.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8713 0.7252 -3.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8172 -1.9668 -2.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9254 -0.7676 -2.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5661 -2.3926 -0.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0472 -1.9666 0.2944 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3416 -1.3344 1.1942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6829 1.5930 -0.9429 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2300 0.6642 1.9139 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8026 2.3089 1.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5613 1.9913 1.8611 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2292 2.7628 0.3164 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7255 -0.1891 0.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8368 2.3216 -0.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3246 1.4997 -1.6289 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2200 2.6748 -0.7169 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1049 0.6838 2.4053 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5542 2.2722 1.7405 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2476 0.7710 3.1003 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7470 2.0316 1.9977 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6772 -0.5176 1.9696 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8551 0.3324 0.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1728 -1.2299 -0.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 -0.1487 -1.5996 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8170 -1.9682 -1.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0339 -2.2307 2.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4969 -2.5354 1.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2226 -4.1189 0.4525 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2752 -1.2459 0.7185 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1963 -0.4740 -2.1002 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7933 -2.0839 -1.5111 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1038 -0.7347 -2.8710 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5617 -1.8792 -1.6650 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5513 1.2107 -2.8433 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1717 1.4282 -2.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0594 2.3360 -1.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7683 1.7157 -0.2358 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 8 9 2 0 8 10 1 0 7 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 25 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 6 15 34 1 0 34 4 1 0 34 7 1 0 32 13 1 0 32 18 1 0 29 19 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 6 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 14 50 1 0 14 51 1 0 14 52 1 0 15 53 1 6 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 18 58 1 1 20 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 23 66 1 1 24 67 1 0 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 28 73 1 0 29 74 1 1 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 34 82 1 6 M END

Standard InCHIKey	HXWLKAXCQLXHML-QUEFYMJYSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-18(2)19-9-14-30(25(33)34)16-15-28(5)20(24(19)30)7-8-22-26(3)12-11-23(32)27(4,17-31)21(26)10-13-29(22,28)6/h19-24,31-32H,1,7-17H2,2-6H3,(H,33,34)/t19-,20+,21+,22+,23-,24-,26-,27-,28+,29+,30-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	2.892 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.822 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.297 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.436	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.839	Fsp³:	0.9
MCE-18:	104.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.843	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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.353	Promiscuous compounds:	0.302

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.441	MDCK Permeability:	-5.123
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	1.0 ? 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%):	0.928	30% Bioavailability (F30%):	0.045
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.889	MRP1:	0.876
Plasma Protein Binding (PPB):	95.603%	Volume Distribution (VD):	-0.281
Fu:	4.735% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.001	BCRP inhibitor:	0.134
BSEP inhibitor:	0.958

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.047	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.605	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.0 ? 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):

4.513

Half-life (T1/2):

0.989

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.045
Human Hepatotoxicity (H-HT):	0.619	Drug-induced Liver Injury (DILI):	0.44
AMES Toxicity:	0.251	Rat Oral Acute Toxicity:	0.405
Maximum Recommended Daily Dose:	0.226	Skin Sensitization:	0.99
Carcinogencity:	0.899	Eye Corrosion:	0.107
Eye Irritation:	0.796	Respiratory Toxicity:	0.899
Drug-induced Neurotoxicity:	0.041	Ototoxicity:	0.689
Hematotoxicity:	0.592	Drug-induced Nephrotoxicity:	0.77
Genotoxicity:	0.3	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.385	Hek293 Cytotoxicity:	0.175
BCF:	0.816 ? 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:	3.462 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.936 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.328 ? 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
NPO45500	Rosmarinus officinalis L.	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC534965 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	23700
0.1-0.2	21988
0.2-0.3	3411
0.3-0.4	546
0.4-0.5	132
0.5-0.6	41
0.6-0.7	23
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC488164
1.0	High Similarity	NPC264005
0.8644	High Similarity	NPC488165
0.8421	Intermediate Similarity	NPC264317
0.8421	Intermediate Similarity	NPC294438
0.7869	Intermediate Similarity	NPC269360
0.7705	Intermediate Similarity	NPC16377
0.7419	Intermediate Similarity	NPC151191
0.7097	Intermediate Similarity	NPC213832
0.6984	Remote Similarity	NPC201655
0.6833	Remote Similarity	NPC68828
0.6825	Remote Similarity	NPC488506
0.6825	Remote Similarity	NPC220498
0.6719	Remote Similarity	NPC195395
0.6667	Remote Similarity	NPC80590
0.6615	Remote Similarity	NPC2783
0.6508	Remote Similarity	NPC192744
0.6462	Remote Similarity	NPC271974
0.6462	Remote Similarity	NPC277399
0.6462	Remote Similarity	NPC247312
0.6406	Remote Similarity	NPC30583
0.6324	Remote Similarity	NPC169933
0.6308	Remote Similarity	NPC24772
0.6308	Remote Similarity	NPC211162
0.6308	Remote Similarity	NPC183374
0.6308	Remote Similarity	NPC291373
0.629	Remote Similarity	NPC246445
0.6269	Remote Similarity	NPC601275
0.6119	Remote Similarity	NPC4309
0.6061	Remote Similarity	NPC476071
0.6029	Remote Similarity	NPC475061
0.6029	Remote Similarity	NPC488213
0.5942	Remote Similarity	NPC160506
0.5942	Remote Similarity	NPC486704
0.5882	Remote Similarity	NPC18064
0.5857	Remote Similarity	NPC478841
0.5857	Remote Similarity	NPC488166
0.5857	Remote Similarity	NPC600004
0.5846	Remote Similarity	NPC472608
0.5806	Remote Similarity	NPC78067
0.5806	Remote Similarity	NPC278091
0.5797	Remote Similarity	NPC474719
0.5758	Remote Similarity	NPC119743
0.5714	Remote Similarity	NPC611139
0.5652	Remote Similarity	NPC57954
0.5634	Remote Similarity	NPC608379
0.5595	Remote Similarity	NPC51947
0.5588	Remote Similarity	NPC30322
0.5513	Remote Similarity	NPC486709
0.5417	Remote Similarity	NPC601176
0.5417	Remote Similarity	NPC607677
0.5325	Remote Similarity	NPC606354
0.5309	Remote Similarity	NPC486699
0.5278	Remote Similarity	NPC61543
0.5278	Remote Similarity	NPC293048
0.5278	Remote Similarity	NPC225585
0.527	Remote Similarity	NPC603461
0.5195	Remote Similarity	NPC602512
0.5181	Remote Similarity	NPC290349
0.5139	Remote Similarity	NPC270768
0.5139	Remote Similarity	NPC59263
0.5139	Remote Similarity	NPC210106
0.5139	Remote Similarity	NPC229281
0.5139	Remote Similarity	NPC121798
0.5139	Remote Similarity	NPC234346
0.5135	Remote Similarity	NPC191412
0.5135	Remote Similarity	NPC114159
0.5135	Remote Similarity	NPC6818
0.5072	Remote Similarity	NPC471900
0.5068	Remote Similarity	NPC252714
0.5067	Remote Similarity	NPC127689
0.5067	Remote Similarity	NPC130520
0.5063	Remote Similarity	NPC605397

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC534965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6085
0.1-0.2	2983
0.2-0.3	70
0.3-0.4	9
0.4-0.5	0
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
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
0.8421	Intermediate Similarity	NPD7520	Phase 1
0.5942	Remote Similarity	NPD8035	Phase 2
0.5357	Remote Similarity	NPD8034	Phase 2

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