NPASS Compound

Structure

NPC255176 OpenBabel07101718312D 35 38 0 0 1 0 0 0 0 0999 V2000 6.7644 2.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6082 0.9814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7902 -0.5817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3478 0.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5896 2.3124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3582 -0.5820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2330 -1.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6906 0.5157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5640 5.6877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5453 0.9814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3891 1.4686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9206 0.0070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2175 -1.5351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1020 -1.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0768 3.1562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5640 2.3124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1866 -1.4332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0768 -0.4801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9192 -1.4154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7644 1.4686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9206 0.9814 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5453 0.0070 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8212 -0.6449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2330 0.9814 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7662 -1.5037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5640 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8172 -0.5307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0768 1.4686 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3891 -0.4801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2330 0.0070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8682 -0.4423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5833 -2.0344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5383 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0768 4.8439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 9 34 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 21 28 1 6 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 13 1 6 0 0 0 23 31 1 0 0 0 0 24 28 1 6 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 32 1 6 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 6 0 0 0 31 8 1 1 0 0 0 31 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.39
Volume:	540.394
LogP:	6.211
LogD:	4.95
LogS:	-5.131
# Rotatable Bonds:	6
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	4.875
Fsp3:	0.903
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.743
MDCK Permeability:	1.7520673281978816e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.344
30% Bioavailability (F30%):	0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	89.73693084716797%
Volume Distribution (VD):	1.085
Pgp-substrate:	3.9450879096984863%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.304
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.214
CYP2C9-substrate:	0.171
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.509
CYP3A4-inhibitor:	0.736
CYP3A4-substrate:	0.647

ADMET: Excretion

Clearance (CL):	7.83
Half-life (T1/2):	0.092

ADMET: Toxicity

hERG Blockers:	0.559
Human Hepatotoxicity (H-HT):	0.564
Drug-inuced Liver Injury (DILI):	0.189
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.64
Maximum Recommended Daily Dose:	0.411
Skin Sensitization:	0.884
Carcinogencity:	0.232
Eye Corrosion:	0.182
Eye Irritation:	0.019
Respiratory Toxicity:	0.961

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC255176

Natural Product ID:	NPC255176
*Common Name:**	Methyl(20S,25)-Epoxy-24Alpha-Hydroxy-3,4-Secodammar-4(28)-En-3-Oate
IUPAC Name:	methyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5S)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-6,9a,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoate
Synonyms:
Standard InCHIKey:	GCHBBBWUFBBCGA-GVEJJQTFSA-N
Standard InCHI:	InChI=1S/C31H52O4/c1-20(2)21-12-18-30(7)24(28(21,5)16-15-26(33)34-9)11-10-22-23(13-17-29(22,30)6)31(8)19-14-25(32)27(3,4)35-31/h21-25,32H,1,10-19H2,2-9H3/t21-,22+,23-,24+,25-,28-,29+,30+,31-/m0/s1
SMILES:	COC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]1[C@]1(C)CC[C@@H](C(O1)(C)C)O)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109471
PubChem CID:	76335699
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]

☑ 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	NP ID	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[534828]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[534828]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[534828]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[534828]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC255176 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1382
0.2-0.3	5941
0.3-0.4	14873
0.4-0.5	6165
0.5-0.6	5573
0.6-0.7	5711
0.7-0.8	2626
0.8-0.85	198
0.85-0.9	33
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.907	High Similarity	NPC254572
0.907	High Similarity	NPC250687
0.907	High Similarity	NPC48824
0.907	High Similarity	NPC229407
0.8977	High Similarity	NPC471747
0.8966	High Similarity	NPC269267
0.8837	High Similarity	NPC475007
0.8736	High Similarity	NPC474174
0.8736	High Similarity	NPC251808
0.871	High Similarity	NPC167974
0.8706	High Similarity	NPC471037
0.8571	High Similarity	NPC174051
0.8571	High Similarity	NPC67831
0.8539	High Similarity	NPC476733
0.8539	High Similarity	NPC215029
0.8539	High Similarity	NPC220498
0.8526	High Similarity	NPC473928
0.8526	High Similarity	NPC94919
0.8523	High Similarity	NPC33768
0.8523	High Similarity	NPC134197
0.8488	Intermediate Similarity	NPC245866
0.8471	Intermediate Similarity	NPC232625
0.8462	Intermediate Similarity	NPC291373
0.8434	Intermediate Similarity	NPC66105
0.8427	Intermediate Similarity	NPC56413
0.8427	Intermediate Similarity	NPC470417
0.8427	Intermediate Similarity	NPC4309
0.8409	Intermediate Similarity	NPC12774
0.8409	Intermediate Similarity	NPC70661
0.8409	Intermediate Similarity	NPC2783
0.8409	Intermediate Similarity	NPC472505
0.8409	Intermediate Similarity	NPC80590
0.8391	Intermediate Similarity	NPC263974
0.8372	Intermediate Similarity	NPC145143
0.8372	Intermediate Similarity	NPC476292
0.8372	Intermediate Similarity	NPC474605
0.837	Intermediate Similarity	NPC277399
0.837	Intermediate Similarity	NPC303863
0.8353	Intermediate Similarity	NPC170038
0.8352	Intermediate Similarity	NPC189520
0.8352	Intermediate Similarity	NPC160506
0.8352	Intermediate Similarity	NPC262870
0.8352	Intermediate Similarity	NPC154101
0.8333	Intermediate Similarity	NPC77001
0.8333	Intermediate Similarity	NPC253618
0.8315	Intermediate Similarity	NPC264005
0.8315	Intermediate Similarity	NPC90652
0.8315	Intermediate Similarity	NPC269360
0.8313	Intermediate Similarity	NPC246445
0.8298	Intermediate Similarity	NPC253586
0.8295	Intermediate Similarity	NPC294438
0.8295	Intermediate Similarity	NPC201655
0.8295	Intermediate Similarity	NPC264317
0.8283	Intermediate Similarity	NPC224414
0.828	Intermediate Similarity	NPC279974
0.828	Intermediate Similarity	NPC205173
0.8261	Intermediate Similarity	NPC287118
0.8261	Intermediate Similarity	NPC473690
0.8261	Intermediate Similarity	NPC471902
0.8242	Intermediate Similarity	NPC471896
0.8235	Intermediate Similarity	NPC118987
0.8222	Intermediate Similarity	NPC211162
0.8222	Intermediate Similarity	NPC183374
0.8222	Intermediate Similarity	NPC474719
0.8222	Intermediate Similarity	NPC16377
0.8214	Intermediate Similarity	NPC238227
0.8202	Intermediate Similarity	NPC155011
0.8202	Intermediate Similarity	NPC324063
0.8182	Intermediate Similarity	NPC287269
0.8172	Intermediate Similarity	NPC240617
0.8163	Intermediate Similarity	NPC471293
0.8163	Intermediate Similarity	NPC223741
0.8161	Intermediate Similarity	NPC311642
0.8161	Intermediate Similarity	NPC164289
0.8161	Intermediate Similarity	NPC100366
0.8161	Intermediate Similarity	NPC242771
0.8161	Intermediate Similarity	NPC170985
0.8152	Intermediate Similarity	NPC475416
0.8152	Intermediate Similarity	NPC219516
0.8152	Intermediate Similarity	NPC471901
0.814	Intermediate Similarity	NPC472853
0.814	Intermediate Similarity	NPC206735
0.814	Intermediate Similarity	NPC476265
0.814	Intermediate Similarity	NPC274522
0.8132	Intermediate Similarity	NPC116146
0.8132	Intermediate Similarity	NPC32830
0.8132	Intermediate Similarity	NPC474570
0.8132	Intermediate Similarity	NPC474889
0.8132	Intermediate Similarity	NPC24772
0.8132	Intermediate Similarity	NPC57954
0.8132	Intermediate Similarity	NPC54689
0.8132	Intermediate Similarity	NPC213832
0.8132	Intermediate Similarity	NPC475921
0.8132	Intermediate Similarity	NPC474704
0.8125	Intermediate Similarity	NPC108371
0.8119	Intermediate Similarity	NPC106760
0.8118	Intermediate Similarity	NPC321690
0.8118	Intermediate Similarity	NPC476732
0.8118	Intermediate Similarity	NPC199965
0.8111	Intermediate Similarity	NPC167877
0.8111	Intermediate Similarity	NPC96496
0.8111	Intermediate Similarity	NPC474684
0.8111	Intermediate Similarity	NPC142361
0.8105	Intermediate Similarity	NPC107243
0.8105	Intermediate Similarity	NPC57416
0.81	Intermediate Similarity	NPC88744
0.81	Intermediate Similarity	NPC295389
0.8095	Intermediate Similarity	NPC476601
0.809	Intermediate Similarity	NPC98270
0.8085	Intermediate Similarity	NPC37787
0.8085	Intermediate Similarity	NPC469599
0.8085	Intermediate Similarity	NPC184848
0.8085	Intermediate Similarity	NPC69548
0.8085	Intermediate Similarity	NPC98639
0.8085	Intermediate Similarity	NPC469329
0.8085	Intermediate Similarity	NPC473415
0.8085	Intermediate Similarity	NPC180557
0.8085	Intermediate Similarity	NPC30677
0.8081	Intermediate Similarity	NPC162033
0.8072	Intermediate Similarity	NPC472945
0.8072	Intermediate Similarity	NPC472944
0.8068	Intermediate Similarity	NPC472744
0.8068	Intermediate Similarity	NPC259173
0.8068	Intermediate Similarity	NPC170862
0.8065	Intermediate Similarity	NPC470376
0.8065	Intermediate Similarity	NPC294263
0.8065	Intermediate Similarity	NPC470375
0.8065	Intermediate Similarity	NPC475061
0.8065	Intermediate Similarity	NPC470224
0.8065	Intermediate Similarity	NPC243866
0.8061	Intermediate Similarity	NPC209298
0.8061	Intermediate Similarity	NPC277074
0.8046	Intermediate Similarity	NPC209318
0.8046	Intermediate Similarity	NPC223330
0.8043	Intermediate Similarity	NPC148414
0.8043	Intermediate Similarity	NPC469400
0.8043	Intermediate Similarity	NPC111585
0.8043	Intermediate Similarity	NPC169933
0.8043	Intermediate Similarity	NPC175628
0.8043	Intermediate Similarity	NPC44240
0.8043	Intermediate Similarity	NPC289213
0.8041	Intermediate Similarity	NPC252614
0.8041	Intermediate Similarity	NPC474327
0.8039	Intermediate Similarity	NPC272242
0.8023	Intermediate Similarity	NPC201459
0.8023	Intermediate Similarity	NPC192744
0.8023	Intermediate Similarity	NPC471475
0.8022	Intermediate Similarity	NPC183546
0.8022	Intermediate Similarity	NPC471900
0.8022	Intermediate Similarity	NPC242864
0.8022	Intermediate Similarity	NPC294480
0.8022	Intermediate Similarity	NPC146937
0.8021	Intermediate Similarity	NPC119036
0.8021	Intermediate Similarity	NPC474793
0.802	Intermediate Similarity	NPC473844
0.802	Intermediate Similarity	NPC218853
0.802	Intermediate Similarity	NPC51947
0.802	Intermediate Similarity	NPC284828
0.802	Intermediate Similarity	NPC91583
0.802	Intermediate Similarity	NPC173905
0.802	Intermediate Similarity	NPC5475
0.802	Intermediate Similarity	NPC240125
0.802	Intermediate Similarity	NPC472216
0.8	Intermediate Similarity	NPC104568
0.8	Intermediate Similarity	NPC73038
0.8	Intermediate Similarity	NPC473168
0.8	Intermediate Similarity	NPC55309
0.8	Intermediate Similarity	NPC469867
0.8	Intermediate Similarity	NPC477919
0.8	Intermediate Similarity	NPC68828
0.8	Intermediate Similarity	NPC256227
0.8	Intermediate Similarity	NPC212843
0.8	Intermediate Similarity	NPC28252
0.8	Intermediate Similarity	NPC200054
0.8	Intermediate Similarity	NPC131665
0.8	Intermediate Similarity	NPC180199
0.8	Intermediate Similarity	NPC255387
0.8	Intermediate Similarity	NPC92139
0.8	Intermediate Similarity	NPC29410
0.8	Intermediate Similarity	NPC59530
0.798	Intermediate Similarity	NPC75531
0.798	Intermediate Similarity	NPC255309
0.798	Intermediate Similarity	NPC301787
0.798	Intermediate Similarity	NPC100955
0.798	Intermediate Similarity	NPC121566
0.798	Intermediate Similarity	NPC149124
0.7979	Intermediate Similarity	NPC47853
0.7978	Intermediate Similarity	NPC475509
0.7978	Intermediate Similarity	NPC165064
0.7959	Intermediate Similarity	NPC473163
0.7957	Intermediate Similarity	NPC150383
0.7957	Intermediate Similarity	NPC250753
0.7957	Intermediate Similarity	NPC26888
0.7957	Intermediate Similarity	NPC23434
0.7955	Intermediate Similarity	NPC148740
0.7955	Intermediate Similarity	NPC477935
0.7955	Intermediate Similarity	NPC102156
0.7955	Intermediate Similarity	NPC477858
0.7955	Intermediate Similarity	NPC477936
0.7952	Intermediate Similarity	NPC279241

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC255176 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1838
0.2-0.3	4046
0.3-0.4	2071
0.4-0.5	506
0.5-0.6	200
0.6-0.7	206
0.7-0.8	111
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8352	Intermediate Similarity	NPD8034	Phase 2
0.8352	Intermediate Similarity	NPD8035	Phase 2
0.8295	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6399	Phase 3
0.7917	Intermediate Similarity	NPD6084	Phase 2
0.7917	Intermediate Similarity	NPD6083	Phase 2
0.7865	Intermediate Similarity	NPD4788	Approved
0.7791	Intermediate Similarity	NPD6116	Phase 1
0.7778	Intermediate Similarity	NPD4786	Approved
0.7765	Intermediate Similarity	NPD3702	Approved
0.7723	Intermediate Similarity	NPD6675	Approved
0.7723	Intermediate Similarity	NPD7128	Approved
0.7723	Intermediate Similarity	NPD6402	Approved
0.7723	Intermediate Similarity	NPD5739	Approved
0.7714	Intermediate Similarity	NPD8133	Approved
0.7674	Intermediate Similarity	NPD6117	Approved
0.7647	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6412	Phase 2
0.7634	Intermediate Similarity	NPD6672	Approved
0.7634	Intermediate Similarity	NPD5737	Approved
0.7619	Intermediate Similarity	NPD8297	Approved
0.7609	Intermediate Similarity	NPD6409	Approved
0.7609	Intermediate Similarity	NPD5330	Approved
0.7609	Intermediate Similarity	NPD7521	Approved
0.7609	Intermediate Similarity	NPD7334	Approved
0.7609	Intermediate Similarity	NPD6684	Approved
0.7609	Intermediate Similarity	NPD7146	Approved
0.7573	Intermediate Similarity	NPD6881	Approved
0.7573	Intermediate Similarity	NPD6899	Approved
0.7573	Intermediate Similarity	NPD7320	Approved
0.7556	Intermediate Similarity	NPD3667	Approved
0.7526	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.7476	Intermediate Similarity	NPD5701	Approved
0.7476	Intermediate Similarity	NPD5697	Approved
0.7475	Intermediate Similarity	NPD5696	Approved
0.7447	Intermediate Similarity	NPD6903	Approved
0.7447	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7290	Approved
0.7429	Intermediate Similarity	NPD7102	Approved
0.7429	Intermediate Similarity	NPD6883	Approved
0.7419	Intermediate Similarity	NPD6098	Approved
0.7404	Intermediate Similarity	NPD6011	Approved
0.7404	Intermediate Similarity	NPD6686	Approved
0.7391	Intermediate Similarity	NPD3133	Approved
0.7391	Intermediate Similarity	NPD3665	Phase 1
0.7391	Intermediate Similarity	NPD3666	Approved
0.7383	Intermediate Similarity	NPD4632	Approved
0.7368	Intermediate Similarity	NPD4753	Phase 2
0.7368	Intermediate Similarity	NPD6904	Approved
0.7368	Intermediate Similarity	NPD6673	Approved
0.7368	Intermediate Similarity	NPD5328	Approved
0.7368	Intermediate Similarity	NPD6080	Approved
0.7358	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8130	Phase 1
0.7358	Intermediate Similarity	NPD6617	Approved
0.7358	Intermediate Similarity	NPD6869	Approved
0.7358	Intermediate Similarity	NPD6650	Approved
0.7358	Intermediate Similarity	NPD6649	Approved
0.7358	Intermediate Similarity	NPD6847	Approved
0.7339	Intermediate Similarity	NPD7115	Discovery
0.7333	Intermediate Similarity	NPD6014	Approved
0.7333	Intermediate Similarity	NPD6013	Approved
0.7333	Intermediate Similarity	NPD7525	Registered
0.7333	Intermediate Similarity	NPD6012	Approved
0.732	Intermediate Similarity	NPD4202	Approved
0.73	Intermediate Similarity	NPD7638	Approved
0.729	Intermediate Similarity	NPD6882	Approved
0.7245	Intermediate Similarity	NPD7748	Approved
0.7238	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3618	Phase 1
0.7228	Intermediate Similarity	NPD7640	Approved
0.7228	Intermediate Similarity	NPD7639	Approved
0.7216	Intermediate Similarity	NPD5281	Approved
0.7216	Intermediate Similarity	NPD6079	Approved
0.7216	Intermediate Similarity	NPD7515	Phase 2
0.7216	Intermediate Similarity	NPD5284	Approved
0.7209	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5777	Approved
0.7209	Intermediate Similarity	NPD6081	Approved
0.72	Intermediate Similarity	NPD7902	Approved
0.72	Intermediate Similarity	NPD4755	Approved
0.7174	Intermediate Similarity	NPD4221	Approved
0.7174	Intermediate Similarity	NPD4223	Phase 3
0.7172	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6319	Approved
0.713	Intermediate Similarity	NPD7507	Approved
0.7128	Intermediate Similarity	NPD5329	Approved
0.7108	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4244	Approved
0.7093	Intermediate Similarity	NPD4245	Approved
0.7093	Intermediate Similarity	NPD4789	Approved
0.7083	Intermediate Similarity	NPD5208	Approved
0.7079	Intermediate Similarity	NPD6933	Approved
0.7059	Intermediate Similarity	NPD4700	Approved
0.7059	Intermediate Similarity	NPD5286	Approved
0.7059	Intermediate Similarity	NPD5285	Approved
0.7059	Intermediate Similarity	NPD4696	Approved
0.7053	Intermediate Similarity	NPD5279	Phase 3
0.7041	Intermediate Similarity	NPD6050	Approved
0.7041	Intermediate Similarity	NPD5693	Phase 1
0.7041	Intermediate Similarity	NPD6411	Approved
0.7027	Intermediate Similarity	NPD6009	Approved
0.7024	Intermediate Similarity	NPD4224	Phase 2
0.7021	Intermediate Similarity	NPD3668	Phase 3
0.7021	Intermediate Similarity	NPD4197	Approved
0.701	Intermediate Similarity	NPD6051	Approved
0.7009	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD5210	Approved
0.699	Remote Similarity	NPD5223	Approved
0.6979	Remote Similarity	NPD7524	Approved
0.6977	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3698	Phase 2
0.6966	Remote Similarity	NPD7339	Approved
0.6966	Remote Similarity	NPD6942	Approved
0.6964	Remote Similarity	NPD6335	Approved
0.6957	Remote Similarity	NPD7604	Phase 2
0.6949	Remote Similarity	NPD7319	Approved
0.6939	Remote Similarity	NPD5692	Phase 3
0.6937	Remote Similarity	NPD6274	Approved
0.6931	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5222	Approved
0.6931	Remote Similarity	NPD4697	Phase 3
0.6931	Remote Similarity	NPD5221	Approved
0.693	Remote Similarity	NPD5983	Phase 2
0.6923	Remote Similarity	NPD5211	Phase 2
0.6923	Remote Similarity	NPD5224	Approved
0.6923	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5226	Approved
0.6923	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD4633	Approved
0.6903	Remote Similarity	NPD7100	Approved
0.6903	Remote Similarity	NPD7101	Approved
0.69	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7900	Approved
0.6897	Remote Similarity	NPD7492	Approved
0.6887	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD6317	Approved
0.6875	Remote Similarity	NPD5205	Approved
0.6875	Remote Similarity	NPD4138	Approved
0.6875	Remote Similarity	NPD4690	Approved
0.6875	Remote Similarity	NPD4688	Approved
0.6875	Remote Similarity	NPD4693	Phase 3
0.6875	Remote Similarity	NPD4689	Approved
0.6869	Remote Similarity	NPD5694	Approved
0.6869	Remote Similarity	NPD7637	Suspended
0.6863	Remote Similarity	NPD5173	Approved
0.686	Remote Similarity	NPD5360	Phase 3
0.686	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5175	Approved
0.6857	Remote Similarity	NPD5174	Approved
0.6857	Remote Similarity	NPD4754	Approved
0.6854	Remote Similarity	NPD6924	Approved
0.6854	Remote Similarity	NPD6926	Approved
0.6842	Remote Similarity	NPD6059	Approved
0.6842	Remote Similarity	NPD6054	Approved
0.6842	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6336	Discontinued
0.6838	Remote Similarity	NPD6616	Approved
0.6837	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6101	Approved
0.6814	Remote Similarity	NPD7327	Approved
0.6814	Remote Similarity	NPD6313	Approved
0.6814	Remote Similarity	NPD7328	Approved
0.6814	Remote Similarity	NPD6314	Approved
0.6809	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6435	Approved
0.6796	Remote Similarity	NPD4225	Approved
0.6792	Remote Similarity	NPD5141	Approved
0.6789	Remote Similarity	NPD4634	Approved
0.6786	Remote Similarity	NPD6868	Approved
0.6783	Remote Similarity	NPD6909	Approved
0.6783	Remote Similarity	NPD6908	Approved
0.6782	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7078	Approved
0.678	Remote Similarity	NPD8293	Discontinued
0.6768	Remote Similarity	NPD5207	Approved
0.6762	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD7516	Approved
0.6739	Remote Similarity	NPD3617	Approved
0.6737	Remote Similarity	NPD5362	Discontinued
0.6737	Remote Similarity	NPD6695	Phase 3
0.6733	Remote Similarity	NPD6001	Approved
0.6729	Remote Similarity	NPD4767	Approved
0.6729	Remote Similarity	NPD4768	Approved
0.6724	Remote Similarity	NPD6370	Approved
0.6723	Remote Similarity	NPD7736	Approved
0.6703	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5369	Approved
0.6702	Remote Similarity	NPD4139	Approved
0.6702	Remote Similarity	NPD4692	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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