NPASS Compound

Structure

NPC469533 OpenBabel07101719252D 30 33 0 0 1 0 0 0 0 0999 V2000 -5.7633 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1161 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4980 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7852 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 -4.6622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 21 2 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 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 13 1 0 0 0 0 12 23 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 21 27 1 0 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 23 28 1 1 0 0 0 24 29 1 0 0 0 0 25 28 1 0 0 0 0 26 29 1 1 0 0 0 27 30 1 1 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.37
Volume:	479.432
LogP:	6.824
LogD:	5.871
LogS:	-6.729
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	4.845
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.897
MDCK Permeability:	1.1868743058585096e-05
Pgp-inhibitor:	0.897
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.77
30% Bioavailability (F30%):	0.38

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	94.01660919189453%
Volume Distribution (VD):	1.404
Pgp-substrate:	1.4097621440887451%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.614
CYP2C19-inhibitor:	0.143
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.365
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.786

ADMET: Excretion

Clearance (CL):	6.266
Half-life (T1/2):	0.021

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.323
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.391
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.169
Carcinogencity:	0.022
Eye Corrosion:	0.042
Eye Irritation:	0.739
Respiratory Toxicity:	0.524

Download Data

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

Natural Product: NPC469533

Natural Product ID:	NPC469533
*Common Name:**	Conicasterol
IUPAC Name:	(3S,9R,10R,13R,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-4-methylidene-1,2,3,5,6,7,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
Synonyms:	Conicasterol
Standard InCHIKey:	BDIHZBORJCSTHA-ZNYUSWPXSA-N
Standard InCHI:	InChI=1S/C29H48O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h18-20,23-24,26-27,30H,5,8-17H2,1-4,6-7H3/t19-,20-,23-,24?,26+,27+,28-,29+/m1/s1
SMILES:	CC([C@@H](CC[C@H]([C@H]1CCC2=C3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H](C(=C)C1CC3)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1085443
PubChem CID:	46881116
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*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
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421754]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193024]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[15679329]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[16441091]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125225]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318032]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[19961178]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078073]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	palau	n.a.	PMID[20078073]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21428459]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23830699]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27213234]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27548648]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29989811]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30346758]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32191460]
NPO22214	Theonella swinhoei	Species	Theonellidae	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	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT76	Cell Line	C6	Rattus norvegicus	IC50	>	70000.0	nM	PMID[541872]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	70000.0	nM	PMID[541872]
NPT1635	Cell Line	H9c2	Rattus norvegicus	IC50	>	70000.0	nM	PMID[541872]

☑ 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 NPC469533 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	147
0.1-0.2	1410
0.2-0.3	7436
0.3-0.4	15930
0.4-0.5	7103
0.5-0.6	5820
0.6-0.7	3537
0.7-0.8	993
0.8-0.85	204
0.85-0.9	83
0.9-0.95	31
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469534
1.0	High Similarity	NPC469593
0.9315	High Similarity	NPC30986
0.9315	High Similarity	NPC209430
0.9296	High Similarity	NPC141071
0.9296	High Similarity	NPC471723
0.9296	High Similarity	NPC257347
0.9178	High Similarity	NPC474216
0.9167	High Similarity	NPC247325
0.9167	High Similarity	NPC189883
0.9167	High Similarity	NPC129165
0.9167	High Similarity	NPC244488
0.9167	High Similarity	NPC134330
0.9054	High Similarity	NPC28862
0.9054	High Similarity	NPC47982
0.9054	High Similarity	NPC143182
0.9054	High Similarity	NPC84694
0.9054	High Similarity	NPC81306
0.9054	High Similarity	NPC109546
0.9028	High Similarity	NPC121744
0.9028	High Similarity	NPC230301
0.9028	High Similarity	NPC304309
0.9028	High Similarity	NPC288035
0.9028	High Similarity	NPC28657
0.9028	High Similarity	NPC162742
0.9028	High Similarity	NPC136188
0.9028	High Similarity	NPC134847
0.9028	High Similarity	NPC22105
0.9028	High Similarity	NPC285893
0.9028	High Similarity	NPC118508
0.9028	High Similarity	NPC322353
0.8933	High Similarity	NPC209944
0.8933	High Similarity	NPC241290
0.8933	High Similarity	NPC234193
0.8933	High Similarity	NPC164840
0.8919	High Similarity	NPC473943
0.8904	High Similarity	NPC300324
0.8904	High Similarity	NPC202642
0.8904	High Similarity	NPC113733
0.8904	High Similarity	NPC321016
0.8904	High Similarity	NPC470362
0.8904	High Similarity	NPC46160
0.8904	High Similarity	NPC321381
0.8904	High Similarity	NPC237460
0.8904	High Similarity	NPC107059
0.8904	High Similarity	NPC240604
0.8904	High Similarity	NPC73875
0.8831	High Similarity	NPC317458
0.8816	High Similarity	NPC264245
0.8816	High Similarity	NPC209620
0.8816	High Similarity	NPC23852
0.88	High Similarity	NPC1319
0.8784	High Similarity	NPC34019
0.8784	High Similarity	NPC155986
0.8784	High Similarity	NPC198968
0.8784	High Similarity	NPC214570
0.8784	High Similarity	NPC318495
0.8767	High Similarity	NPC185536
0.875	High Similarity	NPC182717
0.875	High Similarity	NPC201373
0.8732	High Similarity	NPC145498
0.8718	High Similarity	NPC474047
0.8701	High Similarity	NPC296701
0.8701	High Similarity	NPC49964
0.8701	High Similarity	NPC50964
0.8701	High Similarity	NPC101462
0.8701	High Similarity	NPC202389
0.8701	High Similarity	NPC87489
0.8701	High Similarity	NPC470049
0.8701	High Similarity	NPC189972
0.8701	High Similarity	NPC218616
0.8684	High Similarity	NPC236112
0.8667	High Similarity	NPC138621
0.8667	High Similarity	NPC87604
0.8667	High Similarity	NPC476314
0.8667	High Similarity	NPC76931
0.8667	High Similarity	NPC65897
0.8667	High Similarity	NPC244385
0.8667	High Similarity	NPC85346
0.8667	High Similarity	NPC275910
0.8667	High Similarity	NPC6978
0.8667	High Similarity	NPC186191
0.8667	High Similarity	NPC477522
0.8667	High Similarity	NPC302041
0.8667	High Similarity	NPC307965
0.8667	High Similarity	NPC285761
0.8667	High Similarity	NPC477514
0.8667	High Similarity	NPC205455
0.8667	High Similarity	NPC18603
0.8667	High Similarity	NPC167037
0.8649	High Similarity	NPC253190
0.8649	High Similarity	NPC96319
0.863	High Similarity	NPC306727
0.863	High Similarity	NPC243342
0.863	High Similarity	NPC91858
0.863	High Similarity	NPC477138
0.863	High Similarity	NPC100334
0.8611	High Similarity	NPC111234
0.8611	High Similarity	NPC242001
0.859	High Similarity	NPC475789
0.859	High Similarity	NPC474634
0.8571	High Similarity	NPC474752
0.8571	High Similarity	NPC7505
0.8571	High Similarity	NPC474759
0.8571	High Similarity	NPC474531
0.8571	High Similarity	NPC474683
0.8571	High Similarity	NPC47761
0.8571	High Similarity	NPC82986
0.8571	High Similarity	NPC474731
0.8553	High Similarity	NPC273410
0.8553	High Similarity	NPC80530
0.8553	High Similarity	NPC328714
0.8533	High Similarity	NPC119355
0.8533	High Similarity	NPC470758
0.8533	High Similarity	NPC331618
0.8533	High Similarity	NPC470711
0.8533	High Similarity	NPC257191
0.8533	High Similarity	NPC212241
0.8533	High Similarity	NPC248830
0.8533	High Similarity	NPC91594
0.8514	High Similarity	NPC291503
0.8514	High Similarity	NPC66566
0.8514	High Similarity	NPC477923
0.85	High Similarity	NPC6391
0.85	High Similarity	NPC261266
0.8493	Intermediate Similarity	NPC195489
0.8493	Intermediate Similarity	NPC474140
0.8493	Intermediate Similarity	NPC474743
0.8493	Intermediate Similarity	NPC471799
0.8481	Intermediate Similarity	NPC231310
0.8481	Intermediate Similarity	NPC205845
0.8481	Intermediate Similarity	NPC185568
0.8481	Intermediate Similarity	NPC238485
0.8481	Intermediate Similarity	NPC470077
0.8472	Intermediate Similarity	NPC45296
0.8472	Intermediate Similarity	NPC34834
0.8462	Intermediate Similarity	NPC30166
0.8451	Intermediate Similarity	NPC208999
0.8451	Intermediate Similarity	NPC160209
0.8451	Intermediate Similarity	NPC96484
0.8442	Intermediate Similarity	NPC102253
0.8442	Intermediate Similarity	NPC26117
0.8442	Intermediate Similarity	NPC295131
0.8442	Intermediate Similarity	NPC322313
0.8442	Intermediate Similarity	NPC236237
0.8442	Intermediate Similarity	NPC13554
0.8442	Intermediate Similarity	NPC96362
0.8421	Intermediate Similarity	NPC472342
0.8421	Intermediate Similarity	NPC83351
0.8421	Intermediate Similarity	NPC11908
0.8421	Intermediate Similarity	NPC301707
0.8421	Intermediate Similarity	NPC167891
0.8421	Intermediate Similarity	NPC318136
0.8421	Intermediate Similarity	NPC312328
0.8406	Intermediate Similarity	NPC68656
0.84	Intermediate Similarity	NPC470749
0.84	Intermediate Similarity	NPC27765
0.84	Intermediate Similarity	NPC290598
0.84	Intermediate Similarity	NPC122418
0.84	Intermediate Similarity	NPC30590
0.84	Intermediate Similarity	NPC120098
0.84	Intermediate Similarity	NPC265588
0.84	Intermediate Similarity	NPC274079
0.84	Intermediate Similarity	NPC38141
0.84	Intermediate Similarity	NPC477925
0.84	Intermediate Similarity	NPC265328
0.8378	Intermediate Similarity	NPC254509
0.8378	Intermediate Similarity	NPC25511
0.8378	Intermediate Similarity	NPC196358
0.8378	Intermediate Similarity	NPC62657
0.8378	Intermediate Similarity	NPC471797
0.8378	Intermediate Similarity	NPC145552
0.8378	Intermediate Similarity	NPC476366
0.8378	Intermediate Similarity	NPC201048
0.8378	Intermediate Similarity	NPC476736
0.8378	Intermediate Similarity	NPC192638
0.8378	Intermediate Similarity	NPC5046
0.8378	Intermediate Similarity	NPC49168
0.8375	Intermediate Similarity	NPC266511
0.8375	Intermediate Similarity	NPC470360
0.8375	Intermediate Similarity	NPC318390
0.8375	Intermediate Similarity	NPC274448
0.8356	Intermediate Similarity	NPC167706
0.8356	Intermediate Similarity	NPC164045
0.8356	Intermediate Similarity	NPC110799
0.8354	Intermediate Similarity	NPC82623
0.8354	Intermediate Similarity	NPC470384
0.8333	Intermediate Similarity	NPC9942
0.8333	Intermediate Similarity	NPC249423
0.8333	Intermediate Similarity	NPC470383
0.8333	Intermediate Similarity	NPC476646
0.8312	Intermediate Similarity	NPC472463
0.831	Intermediate Similarity	NPC69649
0.831	Intermediate Similarity	NPC68703
0.831	Intermediate Similarity	NPC197805
0.8293	Intermediate Similarity	NPC133588
0.8293	Intermediate Similarity	NPC474668
0.8289	Intermediate Similarity	NPC34177
0.8289	Intermediate Similarity	NPC157996
0.8289	Intermediate Similarity	NPC471798

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 NPC469533 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1734
0.2-0.3	4476
0.3-0.4	1995
0.4-0.5	381
0.5-0.6	172
0.6-0.7	161
0.7-0.8	53
0.8-0.85	18
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9028	High Similarity	NPD6942	Approved
0.9028	High Similarity	NPD7339	Approved
0.8649	High Similarity	NPD3701	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD7525	Registered
0.8133	Intermediate Similarity	NPD6924	Approved
0.8133	Intermediate Similarity	NPD6926	Approved
0.8108	Intermediate Similarity	NPD7150	Approved
0.8108	Intermediate Similarity	NPD7151	Approved
0.8108	Intermediate Similarity	NPD7152	Approved
0.8108	Intermediate Similarity	NPD4243	Approved
0.8082	Intermediate Similarity	NPD6922	Approved
0.8082	Intermediate Similarity	NPD6923	Approved
0.8077	Intermediate Similarity	NPD7645	Phase 2
0.8077	Intermediate Similarity	NPD6929	Approved
0.8025	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.7975	Intermediate Similarity	NPD6931	Approved
0.7975	Intermediate Similarity	NPD6930	Phase 2
0.7973	Intermediate Similarity	NPD7144	Approved
0.7973	Intermediate Similarity	NPD7143	Approved
0.7952	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD6933	Approved
0.7895	Intermediate Similarity	NPD4785	Approved
0.7895	Intermediate Similarity	NPD4784	Approved
0.7831	Intermediate Similarity	NPD3618	Phase 1
0.7821	Intermediate Similarity	NPD6925	Approved
0.7821	Intermediate Similarity	NPD5776	Phase 2
0.7792	Intermediate Similarity	NPD8264	Approved
0.7765	Intermediate Similarity	NPD5328	Approved
0.775	Intermediate Similarity	NPD4748	Discontinued
0.7722	Intermediate Similarity	NPD7145	Approved
0.7683	Intermediate Similarity	NPD6695	Phase 3
0.759	Intermediate Similarity	NPD3665	Phase 1
0.759	Intermediate Similarity	NPD3133	Approved
0.759	Intermediate Similarity	NPD3666	Approved
0.759	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6079	Approved
0.7564	Intermediate Similarity	NPD5275	Approved
0.7564	Intermediate Similarity	NPD4190	Phase 3
0.7531	Intermediate Similarity	NPD7509	Discontinued
0.7531	Intermediate Similarity	NPD7514	Phase 3
0.75	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6893	Approved
0.7439	Intermediate Similarity	NPD6902	Approved
0.7375	Intermediate Similarity	NPD6932	Approved
0.7326	Intermediate Similarity	NPD7750	Discontinued
0.7326	Intermediate Similarity	NPD7524	Approved
0.7317	Intermediate Similarity	NPD7332	Phase 2
0.7303	Intermediate Similarity	NPD4202	Approved
0.7294	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6898	Phase 1
0.7209	Intermediate Similarity	NPD5279	Phase 3
0.7204	Intermediate Similarity	NPD7640	Approved
0.7204	Intermediate Similarity	NPD7639	Approved
0.7195	Intermediate Similarity	NPD4195	Approved
0.7195	Intermediate Similarity	NPD6683	Phase 2
0.7176	Intermediate Similarity	NPD3668	Phase 3
0.7111	Intermediate Similarity	NPD6399	Phase 3
0.7097	Intermediate Similarity	NPD7638	Approved
0.7065	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5222	Approved
0.7065	Intermediate Similarity	NPD5221	Approved
0.7065	Intermediate Similarity	NPD4697	Phase 3
0.7053	Intermediate Similarity	NPD5211	Phase 2
0.7	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD7087	Discontinued
0.6989	Remote Similarity	NPD4755	Approved
0.6989	Remote Similarity	NPD5173	Approved
0.6966	Remote Similarity	NPD4753	Phase 2
0.6941	Remote Similarity	NPD4223	Phase 3
0.6941	Remote Similarity	NPD4221	Approved
0.6923	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5290	Discontinued
0.6907	Remote Similarity	NPD5141	Approved
0.6897	Remote Similarity	NPD5329	Approved
0.6867	Remote Similarity	NPD3617	Approved
0.686	Remote Similarity	NPD4788	Approved
0.6842	Remote Similarity	NPD5286	Approved
0.6842	Remote Similarity	NPD4700	Approved
0.6842	Remote Similarity	NPD5285	Approved
0.6842	Remote Similarity	NPD4696	Approved
0.6835	Remote Similarity	NPD4787	Phase 1
0.6818	Remote Similarity	NPD7146	Approved
0.6818	Remote Similarity	NPD7521	Approved
0.6818	Remote Similarity	NPD6409	Approved
0.6818	Remote Similarity	NPD7334	Approved
0.6818	Remote Similarity	NPD5330	Approved
0.6818	Remote Similarity	NPD6684	Approved
0.6782	Remote Similarity	NPD4197	Approved
0.6778	Remote Similarity	NPD6051	Approved
0.6771	Remote Similarity	NPD5223	Approved
0.6761	Remote Similarity	NPD342	Phase 1
0.675	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5226	Approved
0.6701	Remote Similarity	NPD5224	Approved
0.6701	Remote Similarity	NPD4633	Approved
0.6701	Remote Similarity	NPD5225	Approved
0.6701	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6633	Remote Similarity	NPD5174	Approved
0.6633	Remote Similarity	NPD5175	Approved
0.6633	Remote Similarity	NPD4754	Approved
0.6632	Remote Similarity	NPD6084	Phase 2
0.6632	Remote Similarity	NPD6083	Phase 2
0.663	Remote Similarity	NPD8035	Phase 2
0.663	Remote Similarity	NPD8034	Phase 2
0.663	Remote Similarity	NPD7637	Suspended
0.6629	Remote Similarity	NPD4519	Discontinued
0.6629	Remote Similarity	NPD5205	Approved
0.6629	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4138	Approved
0.6629	Remote Similarity	NPD4693	Phase 3
0.6629	Remote Similarity	NPD4690	Approved
0.6629	Remote Similarity	NPD4689	Approved
0.6629	Remote Similarity	NPD4623	Approved
0.6629	Remote Similarity	NPD4688	Approved
0.6598	Remote Similarity	NPD4159	Approved
0.6596	Remote Similarity	NPD4629	Approved
0.6596	Remote Similarity	NPD5210	Approved
0.6585	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4225	Approved
0.6535	Remote Similarity	NPD6881	Approved
0.6535	Remote Similarity	NPD6899	Approved
0.6535	Remote Similarity	NPD7320	Approved
0.6522	Remote Similarity	NPD7136	Phase 2
0.6512	Remote Similarity	NPD4695	Discontinued
0.65	Remote Similarity	NPD4768	Approved
0.65	Remote Similarity	NPD4767	Approved
0.6484	Remote Similarity	NPD5737	Approved
0.6484	Remote Similarity	NPD4723	Approved
0.6484	Remote Similarity	NPD6672	Approved
0.6484	Remote Similarity	NPD4722	Approved
0.6471	Remote Similarity	NPD6372	Approved
0.6471	Remote Similarity	NPD6373	Approved
0.6471	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7902	Approved
0.6444	Remote Similarity	NPD4694	Approved
0.6444	Remote Similarity	NPD5690	Phase 2
0.6444	Remote Similarity	NPD5280	Approved
0.6438	Remote Similarity	NPD4219	Approved
0.6437	Remote Similarity	NPD4692	Approved
0.6437	Remote Similarity	NPD4139	Approved
0.6436	Remote Similarity	NPD5697	Approved
0.6436	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD6117	Approved
0.642	Remote Similarity	NPD4245	Approved
0.642	Remote Similarity	NPD4244	Approved
0.6408	Remote Similarity	NPD7102	Approved
0.6408	Remote Similarity	NPD6883	Approved
0.6408	Remote Similarity	NPD7290	Approved
0.6375	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5128	Approved
0.6373	Remote Similarity	NPD5168	Approved
0.6373	Remote Similarity	NPD6011	Approved
0.6373	Remote Similarity	NPD4730	Approved
0.6373	Remote Similarity	NPD4729	Approved
0.6355	Remote Similarity	NPD7115	Discovery
0.6353	Remote Similarity	NPD6116	Phase 1
0.6346	Remote Similarity	NPD6847	Approved
0.6346	Remote Similarity	NPD6649	Approved
0.6346	Remote Similarity	NPD6650	Approved
0.6346	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6617	Approved
0.6346	Remote Similarity	NPD8130	Phase 1
0.6346	Remote Similarity	NPD6869	Approved
0.6311	Remote Similarity	NPD6013	Approved
0.6311	Remote Similarity	NPD6012	Approved
0.6311	Remote Similarity	NPD6014	Approved
0.631	Remote Similarity	NPD3703	Phase 2
0.6296	Remote Similarity	NPD3698	Phase 2
0.6296	Remote Similarity	NPD4137	Phase 3
0.6286	Remote Similarity	NPD6882	Approved
0.6286	Remote Similarity	NPD8297	Approved
0.6279	Remote Similarity	NPD6118	Approved
0.6279	Remote Similarity	NPD6697	Approved
0.6279	Remote Similarity	NPD6114	Approved
0.6279	Remote Similarity	NPD6115	Approved
0.6277	Remote Similarity	NPD6411	Approved
0.6275	Remote Similarity	NPD6412	Phase 2
0.6264	Remote Similarity	NPD6098	Approved
0.625	Remote Similarity	NPD5169	Approved
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD5135	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD5134	Clinical (unspecified phase)

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