NPASS Compound

Structure

NPC244488 OpenBabel07101719522D 28 31 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 4.8363 2.9680 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 2.1913 2.4135 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 4.4762 4.6622 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 0.8660 -1.5000 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 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 -1.7321 0.0000 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 -0.8660 0.5000 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 -1.5000 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 3.8581 2.7601 0.0000 C 0 0 2 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 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 2.5981 0.5000 0.0000 C 0 0 1 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 -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 C 0 0 1 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 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 19 3 1 1 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 28 1 1 0 0 0 22 10 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 27 1 1 0 0 0 24 27 1 1 0 0 0 25 26 1 1 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.35
Volume:	447.476
LogP:	7.507
LogD:	6.362
LogS:	-6.641
# 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:	0.488
Synthetic Accessibility Score:	4.227
Fsp3:	0.926
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:	-4.682
MDCK Permeability:	1.118497493735049e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.638

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.18
Plasma Protein Binding (PPB):	92.66844940185547%
Volume Distribution (VD):	1.434
Pgp-substrate:	1.3070701360702515%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.42
CYP2C19-inhibitor:	0.169
CYP2C19-substrate:	0.909
CYP2C9-inhibitor:	0.28
CYP2C9-substrate:	0.586
CYP2D6-inhibitor:	0.084
CYP2D6-substrate:	0.504
CYP3A4-inhibitor:	0.495
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	6.936
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.786
Human Hepatotoxicity (H-HT):	0.237
Drug-inuced Liver Injury (DILI):	0.804
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.477
Skin Sensitization:	0.949
Carcinogencity:	0.16
Eye Corrosion:	0.227
Eye Irritation:	0.654
Respiratory Toxicity:	0.766

Download Data

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

Natural Product: NPC244488

Natural Product ID:	NPC244488
*Common Name:**	4-Cholesten-3B-Ol
IUPAC Name:	(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	UIMGHSAOLFTOBF-DPAQBDIFSA-N
Standard InCHI:	InChI=1S/C27H46O/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/h17-19,21-25,28H,6-16H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
SMILES:	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498629
PubChem CID:	11452005
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

*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
NPO33255	peyssonnelia sp.	Species	Peyssonneliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21036050]

☑ 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	8

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	50000.0	nM	PMID[548202]
NPT1900	Cell Line	DU-4475	Homo sapiens	IC50	>	25000.0	nM	PMID[548203]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	>	25000.0	nM	PMID[548203]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	25000.0	nM	PMID[548203]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	25000.0	nM	PMID[548203]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	25000.0	nM	PMID[548203]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	25000.0	nM	PMID[548203]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25000.0	nM	PMID[548203]

☑ 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 NPC244488 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	151
0.1-0.2	1326
0.2-0.3	7231
0.3-0.4	15584
0.4-0.5	7339
0.5-0.6	5898
0.6-0.7	3719
0.7-0.8	1119
0.8-0.85	187
0.85-0.9	75
0.9-0.95	58
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC247325
0.9589	High Similarity	NPC143182
0.9589	High Similarity	NPC81306
0.9589	High Similarity	NPC47982
0.9589	High Similarity	NPC30986
0.9589	High Similarity	NPC109546
0.9589	High Similarity	NPC84694
0.9589	High Similarity	NPC209430
0.9589	High Similarity	NPC28862
0.9459	High Similarity	NPC234193
0.9452	High Similarity	NPC474216
0.9333	High Similarity	NPC209620
0.9333	High Similarity	NPC23852
0.9333	High Similarity	NPC264245
0.9306	High Similarity	NPC471723
0.9306	High Similarity	NPC285893
0.9306	High Similarity	NPC162742
0.9306	High Similarity	NPC22105
0.9306	High Similarity	NPC28657
0.9306	High Similarity	NPC136188
0.9306	High Similarity	NPC304309
0.9306	High Similarity	NPC134847
0.9306	High Similarity	NPC257347
0.9306	High Similarity	NPC288035
0.9306	High Similarity	NPC141071
0.9306	High Similarity	NPC230301
0.9211	High Similarity	NPC50964
0.9211	High Similarity	NPC101462
0.9211	High Similarity	NPC49964
0.9211	High Similarity	NPC189972
0.92	High Similarity	NPC241290
0.92	High Similarity	NPC209944
0.92	High Similarity	NPC164840
0.9189	High Similarity	NPC473943
0.9189	High Similarity	NPC477514
0.9178	High Similarity	NPC321016
0.9178	High Similarity	NPC240604
0.9178	High Similarity	NPC134330
0.9178	High Similarity	NPC107059
0.9178	High Similarity	NPC113733
0.9178	High Similarity	NPC129165
0.9178	High Similarity	NPC321381
0.9178	High Similarity	NPC300324
0.9178	High Similarity	NPC189883
0.9167	High Similarity	NPC469593
0.9167	High Similarity	NPC469533
0.9167	High Similarity	NPC469534
0.9091	High Similarity	NPC317458
0.9091	High Similarity	NPC474634
0.9091	High Similarity	NPC475789
0.9079	High Similarity	NPC47761
0.9079	High Similarity	NPC474759
0.9079	High Similarity	NPC7505
0.9079	High Similarity	NPC474731
0.9079	High Similarity	NPC474752
0.9079	High Similarity	NPC474683
0.9079	High Similarity	NPC82986
0.9054	High Similarity	NPC34019
0.9054	High Similarity	NPC198968
0.9054	High Similarity	NPC318495
0.9054	High Similarity	NPC155986
0.9028	High Similarity	NPC474743
0.9028	High Similarity	NPC474140
0.9014	High Similarity	NPC34834
0.9	High Similarity	NPC160209
0.8974	High Similarity	NPC205845
0.8974	High Similarity	NPC185568
0.8974	High Similarity	NPC474047
0.8961	High Similarity	NPC470049
0.8961	High Similarity	NPC87489
0.8961	High Similarity	NPC202389
0.8961	High Similarity	NPC296701
0.8961	High Similarity	NPC218616
0.8933	High Similarity	NPC76931
0.8933	High Similarity	NPC87604
0.8933	High Similarity	NPC477522
0.8933	High Similarity	NPC18603
0.8933	High Similarity	NPC307965
0.8919	High Similarity	NPC237460
0.8919	High Similarity	NPC470362
0.8919	High Similarity	NPC202642
0.8919	High Similarity	NPC46160
0.8861	High Similarity	NPC274448
0.8861	High Similarity	NPC266511
0.8861	High Similarity	NPC471224
0.8846	High Similarity	NPC470384
0.8816	High Similarity	NPC1319
0.8816	High Similarity	NPC328714
0.88	High Similarity	NPC91594
0.88	High Similarity	NPC214570
0.8784	High Similarity	NPC121744
0.8784	High Similarity	NPC322353
0.8784	High Similarity	NPC118508
0.875	High Similarity	NPC475728
0.875	High Similarity	NPC6391
0.875	High Similarity	NPC152808
0.875	High Similarity	NPC293287
0.875	High Similarity	NPC261266
0.8734	High Similarity	NPC238485
0.8734	High Similarity	NPC231310
0.8734	High Similarity	NPC470077
0.8701	High Similarity	NPC236112
0.8701	High Similarity	NPC26117
0.8684	High Similarity	NPC65897
0.8684	High Similarity	NPC138621
0.8684	High Similarity	NPC167037
0.8684	High Similarity	NPC83351
0.8684	High Similarity	NPC244385
0.8684	High Similarity	NPC275910
0.8684	High Similarity	NPC167891
0.8684	High Similarity	NPC85346
0.8684	High Similarity	NPC186191
0.8684	High Similarity	NPC285761
0.8684	High Similarity	NPC302041
0.8684	High Similarity	NPC6978
0.8684	High Similarity	NPC205455
0.8667	High Similarity	NPC96319
0.8667	High Similarity	NPC73875
0.8642	High Similarity	NPC149224
0.863	High Similarity	NPC164045
0.8625	High Similarity	NPC474083
0.8625	High Similarity	NPC470360
0.8625	High Similarity	NPC157257
0.8625	High Similarity	NPC318390
0.8611	High Similarity	NPC474248
0.8608	High Similarity	NPC82623
0.8592	High Similarity	NPC197805
0.8592	High Similarity	NPC68703
0.8592	High Similarity	NPC69649
0.8592	High Similarity	NPC114651
0.859	High Similarity	NPC470383
0.859	High Similarity	NPC474531
0.8571	High Similarity	NPC80530
0.8571	High Similarity	NPC273410
0.8553	High Similarity	NPC470758
0.8553	High Similarity	NPC470711
0.8537	High Similarity	NPC474668
0.8537	High Similarity	NPC133588
0.8533	High Similarity	NPC471468
0.8533	High Similarity	NPC185536
0.8519	High Similarity	NPC299068
0.8519	High Similarity	NPC469994
0.8514	High Similarity	NPC471799
0.8514	High Similarity	NPC472506
0.8514	High Similarity	NPC182717
0.8514	High Similarity	NPC201373
0.8493	Intermediate Similarity	NPC145498
0.8481	Intermediate Similarity	NPC30166
0.8481	Intermediate Similarity	NPC5985
0.8481	Intermediate Similarity	NPC470614
0.8481	Intermediate Similarity	NPC1272
0.8472	Intermediate Similarity	NPC208999
0.8472	Intermediate Similarity	NPC96484
0.8462	Intermediate Similarity	NPC295131
0.8462	Intermediate Similarity	NPC236237
0.8462	Intermediate Similarity	NPC322313
0.8462	Intermediate Similarity	NPC102253
0.8462	Intermediate Similarity	NPC13554
0.8451	Intermediate Similarity	NPC476039
0.8451	Intermediate Similarity	NPC222366
0.8451	Intermediate Similarity	NPC202017
0.8451	Intermediate Similarity	NPC286669
0.8442	Intermediate Similarity	NPC312328
0.8442	Intermediate Similarity	NPC476314
0.8442	Intermediate Similarity	NPC11908
0.8442	Intermediate Similarity	NPC318136
0.8434	Intermediate Similarity	NPC477606
0.8434	Intermediate Similarity	NPC2983
0.8434	Intermediate Similarity	NPC309603
0.8434	Intermediate Similarity	NPC473999
0.8434	Intermediate Similarity	NPC262858
0.8434	Intermediate Similarity	NPC472240
0.8434	Intermediate Similarity	NPC146554
0.8434	Intermediate Similarity	NPC470361
0.8429	Intermediate Similarity	NPC309300
0.8421	Intermediate Similarity	NPC253190
0.8421	Intermediate Similarity	NPC470749
0.8415	Intermediate Similarity	NPC470620
0.84	Intermediate Similarity	NPC201048
0.84	Intermediate Similarity	NPC100334
0.84	Intermediate Similarity	NPC306727
0.84	Intermediate Similarity	NPC27395
0.84	Intermediate Similarity	NPC329090
0.84	Intermediate Similarity	NPC476366
0.84	Intermediate Similarity	NPC471797
0.8378	Intermediate Similarity	NPC111234
0.8378	Intermediate Similarity	NPC242001
0.8375	Intermediate Similarity	NPC470558
0.8375	Intermediate Similarity	NPC134481
0.8356	Intermediate Similarity	NPC471560
0.8356	Intermediate Similarity	NPC167272
0.8356	Intermediate Similarity	NPC269877
0.8354	Intermediate Similarity	NPC476646
0.8333	Intermediate Similarity	NPC295668
0.8333	Intermediate Similarity	NPC48010
0.8333	Intermediate Similarity	NPC3345
0.8333	Intermediate Similarity	NPC171225
0.8333	Intermediate Similarity	NPC11216
0.8333	Intermediate Similarity	NPC291484
0.8333	Intermediate Similarity	NPC80561

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 NPC244488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1575
0.2-0.3	4399
0.3-0.4	2130
0.4-0.5	454
0.5-0.6	178
0.6-0.7	154
0.7-0.8	65
0.8-0.85	27
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9306	High Similarity	NPD6942	Approved
0.9306	High Similarity	NPD7339	Approved
0.8667	High Similarity	NPD3701	Clinical (unspecified phase)
0.863	High Similarity	NPD4243	Approved
0.8462	Intermediate Similarity	NPD7525	Registered
0.8415	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD4784	Approved
0.84	Intermediate Similarity	NPD4785	Approved
0.84	Intermediate Similarity	NPD6926	Approved
0.84	Intermediate Similarity	NPD6924	Approved
0.8356	Intermediate Similarity	NPD6922	Approved
0.8356	Intermediate Similarity	NPD6923	Approved
0.8333	Intermediate Similarity	NPD6929	Approved
0.8272	Intermediate Similarity	NPD4786	Approved
0.8243	Intermediate Similarity	NPD7144	Approved
0.8243	Intermediate Similarity	NPD7143	Approved
0.8228	Intermediate Similarity	NPD6931	Approved
0.8228	Intermediate Similarity	NPD6930	Phase 2
0.8182	Intermediate Similarity	NPD6933	Approved
0.8133	Intermediate Similarity	NPD7152	Approved
0.8133	Intermediate Similarity	NPD7151	Approved
0.8133	Intermediate Similarity	NPD7150	Approved
0.8077	Intermediate Similarity	NPD6925	Approved
0.8077	Intermediate Similarity	NPD5776	Phase 2
0.8052	Intermediate Similarity	NPD5275	Approved
0.8052	Intermediate Similarity	NPD4190	Phase 3
0.8025	Intermediate Similarity	NPD3667	Approved
0.8	Intermediate Similarity	NPD7514	Phase 3
0.7975	Intermediate Similarity	NPD7145	Approved
0.7975	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6695	Phase 3
0.7901	Intermediate Similarity	NPD6902	Approved
0.7875	Intermediate Similarity	NPD7645	Phase 2
0.7831	Intermediate Similarity	NPD3666	Approved
0.7831	Intermediate Similarity	NPD3133	Approved
0.7831	Intermediate Similarity	NPD3665	Phase 1
0.7831	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5328	Approved
0.7778	Intermediate Similarity	NPD7332	Phase 2
0.7738	Intermediate Similarity	NPD6893	Approved
0.7654	Intermediate Similarity	NPD4195	Approved
0.7647	Intermediate Similarity	NPD3618	Phase 1
0.7625	Intermediate Similarity	NPD6932	Approved
0.7614	Intermediate Similarity	NPD6079	Approved
0.7595	Intermediate Similarity	NPD8264	Approved
0.7561	Intermediate Similarity	NPD7509	Discontinued
0.7561	Intermediate Similarity	NPD4748	Discontinued
0.7558	Intermediate Similarity	NPD7750	Discontinued
0.7558	Intermediate Similarity	NPD7524	Approved
0.747	Intermediate Similarity	NPD6898	Phase 1
0.7442	Intermediate Similarity	NPD5279	Phase 3
0.7439	Intermediate Similarity	NPD6683	Phase 2
0.7386	Intermediate Similarity	NPD6051	Approved
0.7386	Intermediate Similarity	NPD4753	Phase 2
0.7381	Intermediate Similarity	NPD4221	Approved
0.7381	Intermediate Similarity	NPD4223	Phase 3
0.7333	Intermediate Similarity	NPD4202	Approved
0.7333	Intermediate Similarity	NPD6399	Phase 3
0.7326	Intermediate Similarity	NPD5329	Approved
0.7286	Intermediate Similarity	NPD342	Phase 1
0.7234	Intermediate Similarity	NPD7640	Approved
0.7234	Intermediate Similarity	NPD7639	Approved
0.7222	Intermediate Similarity	NPD7087	Discontinued
0.7209	Intermediate Similarity	NPD3668	Phase 3
0.7209	Intermediate Similarity	NPD4197	Approved
0.7162	Intermediate Similarity	NPD368	Approved
0.7128	Intermediate Similarity	NPD7638	Approved
0.7126	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5222	Approved
0.7097	Intermediate Similarity	NPD5221	Approved
0.7097	Intermediate Similarity	NPD4697	Phase 3
0.7097	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4788	Approved
0.7083	Intermediate Similarity	NPD5211	Phase 2
0.7045	Intermediate Similarity	NPD7146	Approved
0.7045	Intermediate Similarity	NPD5205	Approved
0.7045	Intermediate Similarity	NPD4138	Approved
0.7045	Intermediate Similarity	NPD5330	Approved
0.7045	Intermediate Similarity	NPD4689	Approved
0.7045	Intermediate Similarity	NPD4688	Approved
0.7045	Intermediate Similarity	NPD6684	Approved
0.7045	Intermediate Similarity	NPD4690	Approved
0.7045	Intermediate Similarity	NPD4623	Approved
0.7045	Intermediate Similarity	NPD6409	Approved
0.7045	Intermediate Similarity	NPD4693	Phase 3
0.7045	Intermediate Similarity	NPD4519	Discontinued
0.7045	Intermediate Similarity	NPD7521	Approved
0.7045	Intermediate Similarity	NPD7334	Approved
0.7033	Intermediate Similarity	NPD7637	Suspended
0.7021	Intermediate Similarity	NPD6083	Phase 2
0.7021	Intermediate Similarity	NPD5173	Approved
0.7021	Intermediate Similarity	NPD4755	Approved
0.7021	Intermediate Similarity	NPD6084	Phase 2
0.6989	Remote Similarity	NPD4629	Approved
0.6989	Remote Similarity	NPD5210	Approved
0.6939	Remote Similarity	NPD5141	Approved
0.6905	Remote Similarity	NPD3617	Approved
0.6905	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5737	Approved
0.6889	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4723	Approved
0.6889	Remote Similarity	NPD6672	Approved
0.6889	Remote Similarity	NPD6903	Approved
0.6889	Remote Similarity	NPD4722	Approved
0.6875	Remote Similarity	NPD5286	Approved
0.6875	Remote Similarity	NPD4700	Approved
0.6875	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD4696	Approved
0.6854	Remote Similarity	NPD4694	Approved
0.6854	Remote Similarity	NPD5280	Approved
0.6854	Remote Similarity	NPD5690	Phase 2
0.6848	Remote Similarity	NPD7515	Phase 2
0.6804	Remote Similarity	NPD5223	Approved
0.6771	Remote Similarity	NPD5290	Discontinued
0.675	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7136	Phase 2
0.6735	Remote Similarity	NPD4633	Approved
0.6735	Remote Similarity	NPD5224	Approved
0.6735	Remote Similarity	NPD5225	Approved
0.6735	Remote Similarity	NPD5226	Approved
0.6712	Remote Similarity	NPD4219	Approved
0.67	Remote Similarity	NPD6402	Approved
0.67	Remote Similarity	NPD5739	Approved
0.67	Remote Similarity	NPD7128	Approved
0.67	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD4747	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6632	Remote Similarity	NPD5695	Phase 3
0.6625	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5696	Approved
0.6585	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD7320	Approved
0.6569	Remote Similarity	NPD6899	Approved
0.6566	Remote Similarity	NPD7632	Discontinued
0.6552	Remote Similarity	NPD4695	Discontinued
0.6543	Remote Similarity	NPD4137	Phase 3
0.6542	Remote Similarity	NPD7115	Discovery
0.6535	Remote Similarity	NPD4767	Approved
0.6535	Remote Similarity	NPD4768	Approved
0.6531	Remote Similarity	NPD6404	Discontinued
0.6526	Remote Similarity	NPD5771	Approved
0.6526	Remote Similarity	NPD7748	Approved
0.6517	Remote Similarity	NPD5362	Discontinued
0.6517	Remote Similarity	NPD5332	Approved
0.6517	Remote Similarity	NPD5331	Approved
0.6505	Remote Similarity	NPD6372	Approved
0.6505	Remote Similarity	NPD6373	Approved
0.6489	Remote Similarity	NPD8034	Phase 2
0.6489	Remote Similarity	NPD5281	Approved
0.6489	Remote Similarity	NPD8035	Phase 2
0.6489	Remote Similarity	NPD5284	Approved
0.6477	Remote Similarity	NPD4790	Discontinued
0.6471	Remote Similarity	NPD6412	Phase 2
0.6471	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD5697	Approved
0.6465	Remote Similarity	NPD4159	Approved
0.6463	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4244	Approved
0.6463	Remote Similarity	NPD4691	Approved
0.6463	Remote Similarity	NPD4789	Approved
0.6463	Remote Similarity	NPD4245	Approved
0.6463	Remote Similarity	NPD6939	Phase 2
0.6456	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6904	Approved
0.6452	Remote Similarity	NPD6080	Approved
0.6452	Remote Similarity	NPD6673	Approved
0.6442	Remote Similarity	NPD6883	Approved
0.6442	Remote Similarity	NPD7290	Approved
0.6442	Remote Similarity	NPD7102	Approved
0.6429	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD5733	Approved
0.6429	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4729	Approved
0.6408	Remote Similarity	NPD4730	Approved
0.6408	Remote Similarity	NPD5128	Approved
0.6408	Remote Similarity	NPD6011	Approved
0.6408	Remote Similarity	NPD5168	Approved
0.6383	Remote Similarity	NPD4096	Approved
0.6381	Remote Similarity	NPD6847	Approved
0.6381	Remote Similarity	NPD6617	Approved
0.6381	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6650	Approved
0.6381	Remote Similarity	NPD6869	Approved
0.6381	Remote Similarity	NPD8130	Phase 1
0.6381	Remote Similarity	NPD6649	Approved
0.6364	Remote Similarity	NPD4821	Approved
0.6364	Remote Similarity	NPD4822	Approved
0.6364	Remote Similarity	NPD4820	Approved
0.6364	Remote Similarity	NPD4819	Approved
0.6346	Remote Similarity	NPD6013	Approved
0.6346	Remote Similarity	NPD6014	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