NPASS Compound

Natural Product: NPC222065

Natural Product ID	NPC222065
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AVSXSVCZWQODGV-OSLSSMLUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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 72 75 0 0 0 0 0 0 0 0999 V2000 5.7063 -4.0687 1.8512 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7601 -2.8287 0.9510 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1457 -1.7853 1.4351 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0426 -0.4537 0.7812 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5535 -0.0827 0.7238 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8290 -0.9857 -0.1881 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2975 -0.8061 -1.6062 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4155 -1.2668 0.0590 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8056 -2.1540 -0.9648 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6407 -2.2100 -0.5389 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8873 -0.9475 0.1621 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8513 -0.0603 -0.6116 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1292 -0.8094 -0.7250 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2662 0.0748 -1.0508 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3013 1.3496 -0.7859 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4976 2.1456 -1.1568 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0253 2.9153 0.0334 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2436 2.6168 1.2846 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7836 2.6946 1.1361 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2047 2.0421 -0.1107 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6705 3.1696 -0.9886 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0765 1.1329 0.3135 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7792 1.8377 0.4735 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4091 1.0704 -0.1563 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4430 -0.2765 0.4428 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5471 -0.0973 1.9824 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8607 4.2688 -0.2508 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4748 -2.9783 -0.3167 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1399 -3.7763 2.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6732 -4.4249 1.9506 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3177 -4.8817 1.4170 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6325 -1.8836 2.4167 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5850 0.2746 1.4272 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5074 -0.5197 -0.2095 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2302 -0.2025 1.8047 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5481 0.9980 0.4521 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3309 -2.0260 0.0597 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1611 0.2963 -1.8669 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3701 -0.9591 -1.7497 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7711 -1.4230 -2.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4500 -1.9972 0.9944 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2781 -3.1725 -0.9839 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8047 -1.7285 -2.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8369 -3.0969 0.1231 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2442 -2.3770 -1.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4228 -1.1696 1.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5043 0.2234 -1.6096 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1162 -1.6082 -1.4980 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2966 -1.3692 0.2355 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1685 -0.3893 -1.5505 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2800 1.4543 -1.5467 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2469 2.8300 -1.9714 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0955 2.7099 0.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5920 3.2461 2.1233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5249 1.5608 1.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3002 2.2847 2.0614 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5076 3.7742 1.1022 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3641 4.0336 -0.3630 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4951 3.5267 -1.6194 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8911 2.8165 -1.7024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3864 0.6837 1.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5464 2.0600 1.5463 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7933 2.8088 -0.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2727 1.1231 -1.2294 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2930 1.6668 0.2174 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0625 -1.0069 2.4107 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4520 -0.0944 2.4563 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0416 0.8500 2.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6587 4.5106 -0.8255 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8919 -2.6017 -1.1692 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4658 -2.4561 -0.3313 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6841 -4.0753 -0.5363 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 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 2 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 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 17 27 1 0 2 28 1 0 25 8 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 29 1 0 1 30 1 0 1 31 1 0 3 32 1 0 4 33 1 0 4 34 1 0 5 35 1 0 5 36 1 0 6 37 1 1 7 38 1 0 7 39 1 0 7 40 1 0 8 41 1 1 9 42 1 0 9 43 1 0 10 44 1 0 10 45 1 0 11 46 1 1 12 47 1 6 13 48 1 0 13 49 1 0 14 50 1 0 16 51 1 0 16 52 1 0 17 53 1 1 18 54 1 0 18 55 1 0 19 56 1 0 19 57 1 0 21 58 1 0 21 59 1 0 21 60 1 0 22 61 1 1 23 62 1 0 23 63 1 0 24 64 1 0 24 65 1 0 26 66 1 0 26 67 1 0 26 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 M END

Standard InCHIKey	AVSXSVCZWQODGV-OSLSSMLUSA-N
Standard InCHI	InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27+/m0/s1
SMILES	CC(=CCC[C@H](C)[C@@H]1CC[C@@H]2[C@H]3CC=C4C[C@@H](CC[C@@]4(C)[C@@H]3CC[C@]12C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	384.34	Volume:	444.84 ? Van der Waals volume.
Dense:	0.864	LogP:	6.649 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.94 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.623 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	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:	0.504	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.3	Fsp³:	0.852
MCE-18:	67.6 ? 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:	0.924	Fluc inhibitor:	0.004 ? 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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.726	Promiscuous compounds:	0.174

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.822	MDCK Permeability:	-4.865
Pgp-inhibitor:	0.982	Pgp-substrate:	0.315
PAMPA:	0.097 ? 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%):	0.429	30% Bioavailability (F30%):	0.071
50% Bioavailability (F50%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803	MRP1:	0.99
Plasma Protein Binding (PPB):	97.835%	Volume Distribution (VD):	-0.032
Fu:	2.746% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.975
OATP1B3 inhibitor:	0.485	BCRP inhibitor:	0.168
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.1	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.071 ? 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):

11.116

Half-life (T1/2):

0.221

ADMET: Toxicity

hERG Blockers:	0.123	hERG Blockers (10um):	0.364
Human Hepatotoxicity (H-HT):	0.469	Drug-induced Liver Injury (DILI):	0.175
AMES Toxicity:	0.393	Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.463	Skin Sensitization:	0.978
Carcinogencity:	0.78	Eye Corrosion:	0.125
Eye Irritation:	0.794	Respiratory Toxicity:	0.89
Drug-induced Neurotoxicity:	0.262	Ototoxicity:	0.458
Hematotoxicity:	0.513	Drug-induced Nephrotoxicity:	0.657
Genotoxicity:	0.07	RPMI-8226 Immunitoxicity:	0.067
A549 Cytotoxicity:	0.823	Hek293 Cytotoxicity:	0.529
BCF:	2.7 ? 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:	4.463 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.227 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.143 ? 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
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22281186]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26394911]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588326]
NPO14041	Dendrobium findlayanum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29338260]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39407585]
NPO22452	Leucanthemum vulgare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14041	Dendrobium findlayanum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22452	Leucanthemum vulgare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14041	Dendrobium findlayanum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22452	Leucanthemum vulgare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14041	Dendrobium findlayanum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	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

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 NPC222065 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	22986
0.1-0.2	22364
0.2-0.3	4016
0.3-0.4	331
0.4-0.5	80
0.5-0.6	36
0.6-0.7	16
0.7-0.8	0
0.8-0.85	9
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	NPC22105
0.8511	High Similarity	NPC162742
0.8511	High Similarity	NPC304309
0.8511	High Similarity	NPC470228
0.8333	Intermediate Similarity	NPC34019
0.8333	Intermediate Similarity	NPC107059
0.8163	Intermediate Similarity	NPC136188
0.8163	Intermediate Similarity	NPC28657
0.8163	Intermediate Similarity	NPC474216
0.8	Intermediate Similarity	NPC230301
0.8	Intermediate Similarity	NPC198968
0.8	Intermediate Similarity	NPC285893
0.8	Intermediate Similarity	NPC134847
0.7843	Intermediate Similarity	NPC241290
0.7843	Intermediate Similarity	NPC164840
0.7843	Intermediate Similarity	NPC484739
0.7843	Intermediate Similarity	NPC209944
0.7843	Intermediate Similarity	NPC264245
0.7843	Intermediate Similarity	NPC155986
0.7692	Intermediate Similarity	NPC321381
0.7547	Intermediate Similarity	NPC59453
0.7407	Intermediate Similarity	NPC603646
0.7273	Intermediate Similarity	NPC473943
0.7255	Intermediate Similarity	NPC600590
0.7222	Intermediate Similarity	NPC472265
0.7143	Intermediate Similarity	NPC488870
0.7115	Intermediate Similarity	NPC154330
0.6981	Remote Similarity	NPC113733
0.6964	Remote Similarity	NPC155011
0.6923	Remote Similarity	NPC221758
0.6842	Remote Similarity	NPC47761
0.6607	Remote Similarity	NPC33913
0.6545	Remote Similarity	NPC51014
0.6429	Remote Similarity	NPC328714
0.6379	Remote Similarity	NPC243985
0.6379	Remote Similarity	NPC280710
0.6379	Remote Similarity	NPC240650
0.6316	Remote Similarity	NPC318495
0.6275	Remote Similarity	NPC96319
0.6271	Remote Similarity	NPC474164
0.6207	Remote Similarity	NPC477522
0.6182	Remote Similarity	NPC328313
0.614	Remote Similarity	NPC87604
0.5968	Remote Similarity	NPC601043
0.5968	Remote Similarity	NPC605412
0.5763	Remote Similarity	NPC1272
0.5763	Remote Similarity	NPC470614
0.5714	Remote Similarity	NPC151519
0.5614	Remote Similarity	NPC20688
0.5536	Remote Similarity	NPC81306
0.5517	Remote Similarity	NPC76879
0.541	Remote Similarity	NPC474752
0.541	Remote Similarity	NPC474683
0.5345	Remote Similarity	NPC109546
0.5345	Remote Similarity	NPC317458
0.5345	Remote Similarity	NPC47982
0.5333	Remote Similarity	NPC31564
0.5333	Remote Similarity	NPC145879
0.5254	Remote Similarity	NPC84694
0.5254	Remote Similarity	NPC28862
0.5254	Remote Similarity	NPC143182
0.5231	Remote Similarity	NPC176012
0.5167	Remote Similarity	NPC317927
0.5152	Remote Similarity	NPC5985
0.5147	Remote Similarity	NPC235126
0.5147	Remote Similarity	NPC309493
0.5147	Remote Similarity	NPC242419
0.5085	Remote Similarity	NPC189972
0.5082	Remote Similarity	NPC26959
0.5079	Remote Similarity	NPC475789
0.5077	Remote Similarity	NPC474970
0.5077	Remote Similarity	NPC474349
0.5077	Remote Similarity	NPC474189
0.5075	Remote Similarity	NPC91604
0.5072	Remote Similarity	NPC147835
0.5072	Remote Similarity	NPC253645
0.5072	Remote Similarity	NPC85001
0.5072	Remote Similarity	NPC95920
0.507	Remote Similarity	NPC3715

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC222065 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7679
0.1-0.2	1300
0.2-0.3	130
0.3-0.4	34
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8163	Intermediate Similarity	NPD6942	Phase 4
0.8	Intermediate Similarity	NPD7339	Approved
0.6923	Remote Similarity	NPD4786	Phase 1
0.6275	Remote Similarity	NPD3701	Pre-clinical
0.5714	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