NPASS Compound

Natural Product: NPC67267

Natural Product ID	NPC67267
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZTJFINKUHDHOSM-OJRBQCEJSA-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:0002031] Stigmastanes 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 76 79 0 0 0 0 0 0 0 0999 V2000 -7.4207 -0.9731 -1.2214 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9220 -1.0317 -0.8921 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7953 -0.6869 0.5555 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3825 -0.7036 1.0306 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3834 -0.9636 0.1944 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9551 -0.9891 0.6335 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5313 -2.4115 0.5389 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2149 0.0180 -0.1141 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2323 -0.2043 -1.5904 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0028 -1.0584 -1.7769 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0128 -0.5259 -0.7558 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0617 0.2032 -1.5287 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8820 -0.7929 -2.2857 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2840 -0.8852 -1.8991 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8645 -0.1831 -0.9649 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3365 -0.3668 -0.6477 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3953 -0.6680 0.8123 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5578 0.1774 1.6954 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0946 0.3009 1.2423 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1289 0.8035 -0.1661 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0015 2.0763 -0.1088 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8441 1.2301 -0.7848 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9810 2.0912 0.0938 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5057 1.7395 -0.0388 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2141 0.2786 0.1912 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4726 0.0199 1.6547 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7126 -0.5705 1.2517 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3695 0.6418 0.7972 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4207 0.7745 1.5694 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7601 1.8409 0.1668 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4870 -1.1172 -2.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8699 -1.8766 -0.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8668 -0.0289 -0.8881 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5922 -2.0472 -1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3622 -0.3286 -1.5542 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3370 -1.4649 1.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1177 -0.5090 2.0535 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6580 -1.1629 -0.8312 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9636 -0.7194 1.7304 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0241 -2.9383 1.4139 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4813 -2.6435 0.6077 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9542 -2.9435 -0.3465 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7655 1.0012 0.0372 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0864 0.7713 -2.1410 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1296 -0.6563 -2.0101 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1613 -2.1269 -1.7047 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3532 -0.8628 -2.8108 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4031 -1.4174 -0.2312 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4855 0.7678 -2.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8778 -0.5803 -3.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3664 -1.8092 -2.2645 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9145 -1.6090 -2.4389 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9638 0.4311 -1.0197 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7036 -1.3003 -1.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0638 -1.7363 0.9400 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4963 -0.3287 2.6883 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0070 1.1665 1.9169 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6513 -0.6947 1.3662 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6497 0.9727 1.9848 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5729 2.8205 0.5771 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0538 1.8729 0.0302 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8920 2.5218 -1.1404 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2075 1.9495 -1.6024 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3104 2.1336 1.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9991 3.1873 -0.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1759 2.0925 -1.0311 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0228 2.3764 0.7206 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3201 0.6170 2.0588 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3930 0.4007 2.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7247 -1.0333 1.8909 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7105 -0.3951 2.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8679 -0.0855 2.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8422 1.7452 1.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3836 1.6298 -0.8556 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9331 2.1788 0.8213 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5623 2.5977 0.0466 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 2 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 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 17 27 1 0 3 28 1 0 28 29 2 0 28 30 1 0 25 8 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 2 35 1 0 3 36 1 1 4 37 1 0 5 38 1 0 6 39 1 1 7 40 1 0 7 41 1 0 7 42 1 0 8 43 1 6 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 1 12 49 1 6 13 50 1 0 13 51 1 0 14 52 1 0 16 53 1 0 16 54 1 0 17 55 1 6 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 6 23 64 1 0 23 65 1 0 24 66 1 0 24 67 1 0 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 M END

Standard InCHIKey	ZTJFINKUHDHOSM-OJRBQCEJSA-N
Standard InCHI	InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,20-21,23-27,30H,2,7,11-18H2,1,3-6H3/b9-8+/t20-,21+,23+,24+,25+,26+,27-,28+,29+/m1/s1
SMILES	CC[C@@H](/C=C/[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(=C)C

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO737	Aspergillus japonicus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO9461	Gmelina leichhardtii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO395	Teucrium pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8403	Annona coriacea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7322	Plagiochila acanthophylla	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10101	Rothmannia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO737	Aspergillus japonicus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12045	Schottera nicaeensis	Species	Phyllophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3670	Crotalaria podocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7322	Plagiochila acanthophylla	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12761	Rheum hotaoense	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9015	Solanum arundo	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3313	Crotalaria trichotoma	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12761	Rheum hotaoense	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO395	Teucrium pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12045	Schottera nicaeensis	Species	Phyllophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5310	Eucalyptus bakeri	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7322	Plagiochila acanthophylla	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4919	Kalanchoe daigremontiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11540	Acacia leptostachya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3313	Crotalaria trichotoma	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13095	Pachycereus tehuantepecanus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10101	Rothmannia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12761	Rheum hotaoense	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9887	Protohermes grandis	Species	Corydalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9461	Gmelina leichhardtii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4454	Maytenus salicifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3670	Crotalaria podocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17461	Hedera canariensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO737	Aspergillus japonicus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO395	Teucrium pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9015	Solanum arundo	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8403	Annona coriacea	Species	Annonaceae	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 NPC67267 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	22750
0.1-0.2	23772
0.2-0.3	2967
0.3-0.4	236
0.4-0.5	71
0.5-0.6	15
0.6-0.7	32
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.84	Intermediate Similarity	NPC113733
0.82	Intermediate Similarity	NPC154330
0.7358	Intermediate Similarity	NPC285893
0.7273	Intermediate Similarity	NPC33913
0.7115	Intermediate Similarity	NPC162742
0.7115	Intermediate Similarity	NPC304309
0.7115	Intermediate Similarity	NPC470228
0.7037	Intermediate Similarity	NPC230301
0.6981	Remote Similarity	NPC22105
0.6981	Remote Similarity	NPC34019
0.6981	Remote Similarity	NPC107059
0.6981	Remote Similarity	NPC600590
0.6852	Remote Similarity	NPC136188
0.6852	Remote Similarity	NPC28657
0.6852	Remote Similarity	NPC474216
0.6727	Remote Similarity	NPC198968
0.6727	Remote Similarity	NPC134847
0.6667	Remote Similarity	NPC221758
0.6607	Remote Similarity	NPC241290
0.6607	Remote Similarity	NPC164840
0.6607	Remote Similarity	NPC484739
0.6607	Remote Similarity	NPC209944
0.6607	Remote Similarity	NPC264245
0.6607	Remote Similarity	NPC155986
0.6491	Remote Similarity	NPC328714
0.6491	Remote Similarity	NPC321381
0.6379	Remote Similarity	NPC472265
0.6379	Remote Similarity	NPC318495
0.6379	Remote Similarity	NPC59453
0.6316	Remote Similarity	NPC51014
0.6271	Remote Similarity	NPC603646
0.6167	Remote Similarity	NPC243985
0.6167	Remote Similarity	NPC473943
0.6167	Remote Similarity	NPC280710
0.6167	Remote Similarity	NPC240650
0.6167	Remote Similarity	NPC155011
0.6066	Remote Similarity	NPC474164
0.6066	Remote Similarity	NPC47761
0.6066	Remote Similarity	NPC488870
0.6038	Remote Similarity	NPC96319
0.5965	Remote Similarity	NPC328313
0.5833	Remote Similarity	NPC1272
0.5833	Remote Similarity	NPC470614
0.5781	Remote Similarity	NPC601043
0.5781	Remote Similarity	NPC605412
0.5763	Remote Similarity	NPC234193
0.5738	Remote Similarity	NPC58063
0.5738	Remote Similarity	NPC477522
0.5593	Remote Similarity	NPC76879
0.5517	Remote Similarity	NPC151519
0.5424	Remote Similarity	NPC20688
0.5385	Remote Similarity	NPC474349
0.5385	Remote Similarity	NPC474189
0.5161	Remote Similarity	NPC87604
0.5075	Remote Similarity	NPC176012

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC67267 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7601
0.1-0.2	1391
0.2-0.3	130
0.3-0.4	21
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
0.7-0.8	1
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
0.7037	Intermediate Similarity	NPD7339	Approved
0.6852	Remote Similarity	NPD6942	Phase 4
0.6667	Remote Similarity	NPD4786	Phase 1
0.6038	Remote Similarity	NPD3701	Pre-clinical
0.5517	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