NPASS Compound

Structure

NPC1272 OpenBabel07101718222D 31 34 0 0 1 0 0 0 0 0999 V2000 -1.5180 4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 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 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -0.9000 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 3.4641 -1.0000 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 4.1132 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 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 -3.4743 5.2722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 1.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 18 2 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 1 1 6 0 0 0 17 2 1 6 0 0 0 17 23 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 29 1 6 0 0 0 20 7 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 26 1 6 0 0 0 22 27 1 6 0 0 0 23 30 1 6 0 0 0 24 25 1 0 0 0 0 24 31 1 6 0 0 0 25 27 1 6 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.34
Volume:	473.847
LogP:	4.14
LogD:	4.077
LogS:	-4.335
# Rotatable Bonds:	6
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	4.852
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.795
MDCK Permeability:	7.097520210663788e-06
Pgp-inhibitor:	0.917
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.888
30% Bioavailability (F30%):	0.381

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.3
Plasma Protein Binding (PPB):	89.80095672607422%
Volume Distribution (VD):	0.862
Pgp-substrate:	3.541083574295044%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.272
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.721
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.509
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	12.163
Half-life (T1/2):	0.381

ADMET: Toxicity

hERG Blockers:	0.115
Human Hepatotoxicity (H-HT):	0.459
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.927
Carcinogencity:	0.618
Eye Corrosion:	0.135
Eye Irritation:	0.06
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC1272

Natural Product ID:	NPC1272
*Common Name:**	(3S,8S,9S,10R,13S,14S,16S,17R)-17-[(2S,3S,6R)-3,7-Dihydroxy-6-Methylheptan-2-Yl]-10,13-Dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-Dodecahydro-1H-Cyclopenta[A]Phenanthrene-3,16-Diol
IUPAC Name:	(3S,8S,9S,10R,13S,14S,16S,17R)-17-[(2S,3S,6R)-3,7-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol
Synonyms:
Standard InCHIKey:	HJMSZKKOQIZOLJ-XPMUQOCRSA-N
Standard InCHI:	InChI=1S/C27H46O4/c1-16(15-28)5-8-23(30)17(2)25-24(31)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-25,28-31H,5,7-15H2,1-4H3/t16-,17-,19+,20-,21+,22+,23+,24+,25+,26+,27+/m1/s1
SMILES:	C[C@H](CC[C@@H]([C@@H](C)[C@H]1[C@H](C[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2088136
PubChem CID:	70695378
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001110] Tetrahydroxy bile acids, alcohols 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
NPO33234	chamaellirium luteum	Species	n.a.	n.a.	roots	sourced from Botanical Liaisons Ltd. (USA) and Blessed Herbs Ltd. (USA)	n.a.	PMID[22880631]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1523	Cell Line	NFF	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[534550]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[534550]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[534550]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[534550]
NPT1524	Cell Line	MM96L	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[534550]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[534550]

☑ 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 NPC1272 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	159
0.1-0.2	1379
0.2-0.3	6000
0.3-0.4	15902
0.4-0.5	7214
0.5-0.6	5716
0.6-0.7	4598
0.7-0.8	1398
0.8-0.85	202
0.85-0.9	90
0.9-0.95	35
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470614
0.9744	High Similarity	NPC124172
0.9737	High Similarity	NPC26117
0.95	High Similarity	NPC24277
0.9474	High Similarity	NPC477522
0.9474	High Similarity	NPC87604
0.9367	High Similarity	NPC110778
0.9268	High Similarity	NPC470542
0.9259	High Similarity	NPC152808
0.9259	High Similarity	NPC293287
0.925	High Similarity	NPC475798
0.925	High Similarity	NPC127606
0.925	High Similarity	NPC209802
0.9211	High Similarity	NPC96319
0.9211	High Similarity	NPC321016
0.9211	High Similarity	NPC107059
0.9211	High Similarity	NPC321381
0.9157	High Similarity	NPC105495
0.9146	High Similarity	NPC271967
0.9125	High Similarity	NPC193870
0.9125	High Similarity	NPC141941
0.9125	High Similarity	NPC477818
0.9114	High Similarity	NPC209620
0.9114	High Similarity	NPC23852
0.9114	High Similarity	NPC470383
0.9103	High Similarity	NPC1319
0.9091	High Similarity	NPC155986
0.9091	High Similarity	NPC198968
0.9091	High Similarity	NPC318495
0.9079	High Similarity	NPC136188
0.9079	High Similarity	NPC162742
0.9079	High Similarity	NPC285893
0.9079	High Similarity	NPC22105
0.9079	High Similarity	NPC134847
0.9079	High Similarity	NPC230301
0.9079	High Similarity	NPC304309
0.9079	High Similarity	NPC28657
0.9079	High Similarity	NPC288035
0.9036	High Similarity	NPC2158
0.9024	High Similarity	NPC201273
0.9	High Similarity	NPC50964
0.8987	High Similarity	NPC71535
0.8987	High Similarity	NPC78545
0.8974	High Similarity	NPC474216
0.8974	High Similarity	NPC477514
0.8974	High Similarity	NPC473943
0.8961	High Similarity	NPC240604
0.8961	High Similarity	NPC300324
0.8961	High Similarity	NPC113733
0.8902	High Similarity	NPC474189
0.8902	High Similarity	NPC474349
0.8861	High Similarity	NPC28862
0.8861	High Similarity	NPC47982
0.8861	High Similarity	NPC328714
0.8861	High Similarity	NPC109546
0.8861	High Similarity	NPC143182
0.8861	High Similarity	NPC84694
0.8861	High Similarity	NPC81306
0.8846	High Similarity	NPC34019
0.8831	High Similarity	NPC141071
0.8831	High Similarity	NPC471723
0.8831	High Similarity	NPC257347
0.8824	High Similarity	NPC107189
0.8816	High Similarity	NPC474140
0.881	High Similarity	NPC475664
0.881	High Similarity	NPC474668
0.8795	High Similarity	NPC261266
0.8795	High Similarity	NPC6605
0.8795	High Similarity	NPC6391
0.8795	High Similarity	NPC139724
0.8765	High Similarity	NPC101462
0.8765	High Similarity	NPC248886
0.8765	High Similarity	NPC201852
0.875	High Similarity	NPC102253
0.875	High Similarity	NPC322313
0.875	High Similarity	NPC241290
0.875	High Similarity	NPC236237
0.875	High Similarity	NPC209944
0.875	High Similarity	NPC164840
0.875	High Similarity	NPC234193
0.8734	High Similarity	NPC167037
0.8734	High Similarity	NPC307965
0.8734	High Similarity	NPC477817
0.8734	High Similarity	NPC477819
0.8734	High Similarity	NPC18603
0.8734	High Similarity	NPC76931
0.8734	High Similarity	NPC244385
0.8734	High Similarity	NPC275910
0.8734	High Similarity	NPC6978
0.8734	High Similarity	NPC138621
0.8718	High Similarity	NPC189883
0.8718	High Similarity	NPC134330
0.8718	High Similarity	NPC129165
0.869	High Similarity	NPC186145
0.869	High Similarity	NPC474657
0.869	High Similarity	NPC475313
0.8675	High Similarity	NPC318390
0.8659	High Similarity	NPC232023
0.8659	High Similarity	NPC474634
0.8642	High Similarity	NPC264245
0.8642	High Similarity	NPC474531
0.8642	High Similarity	NPC47761
0.8642	High Similarity	NPC474683
0.8642	High Similarity	NPC474731
0.8642	High Similarity	NPC474752
0.8642	High Similarity	NPC7505
0.8642	High Similarity	NPC82986
0.8642	High Similarity	NPC474759
0.8625	High Similarity	NPC30986
0.8625	High Similarity	NPC80530
0.8625	High Similarity	NPC472463
0.8625	High Similarity	NPC273410
0.8625	High Similarity	NPC209430
0.8621	High Similarity	NPC242419
0.8621	High Similarity	NPC98193
0.8621	High Similarity	NPC235126
0.8608	High Similarity	NPC471798
0.8608	High Similarity	NPC214570
0.8605	High Similarity	NPC473956
0.8605	High Similarity	NPC475751
0.8571	High Similarity	NPC471799
0.8571	High Similarity	NPC94462
0.8554	High Similarity	NPC255882
0.8554	High Similarity	NPC205845
0.8554	High Similarity	NPC478102
0.8554	High Similarity	NPC185568
0.8539	High Similarity	NPC304899
0.8539	High Similarity	NPC253115
0.8537	High Similarity	NPC20853
0.8537	High Similarity	NPC30166
0.8537	High Similarity	NPC189972
0.8537	High Similarity	NPC49964
0.8537	High Similarity	NPC5985
0.8523	High Similarity	NPC111015
0.8519	High Similarity	NPC236112
0.8519	High Similarity	NPC47149
0.8506	High Similarity	NPC41554
0.8506	High Similarity	NPC97404
0.85	High Similarity	NPC285761
0.8488	Intermediate Similarity	NPC109744
0.8488	Intermediate Similarity	NPC470361
0.8481	Intermediate Similarity	NPC247325
0.8481	Intermediate Similarity	NPC202642
0.8481	Intermediate Similarity	NPC470362
0.8481	Intermediate Similarity	NPC73875
0.8481	Intermediate Similarity	NPC274079
0.8481	Intermediate Similarity	NPC237460
0.8481	Intermediate Similarity	NPC244488
0.8481	Intermediate Similarity	NPC477925
0.8481	Intermediate Similarity	NPC46160
0.8462	Intermediate Similarity	NPC471797
0.8452	Intermediate Similarity	NPC266511
0.8444	Intermediate Similarity	NPC177818
0.8444	Intermediate Similarity	NPC475032
0.8444	Intermediate Similarity	NPC475033
0.8444	Intermediate Similarity	NPC190554
0.8434	Intermediate Similarity	NPC317458
0.8434	Intermediate Similarity	NPC113978
0.8434	Intermediate Similarity	NPC475789
0.8434	Intermediate Similarity	NPC207013
0.8415	Intermediate Similarity	NPC476646
0.8395	Intermediate Similarity	NPC24504
0.8391	Intermediate Similarity	NPC295668
0.8391	Intermediate Similarity	NPC291484
0.8391	Intermediate Similarity	NPC3345
0.8391	Intermediate Similarity	NPC80561
0.8391	Intermediate Similarity	NPC204188
0.8391	Intermediate Similarity	NPC11216
0.8391	Intermediate Similarity	NPC329596
0.8375	Intermediate Similarity	NPC130136
0.8372	Intermediate Similarity	NPC470612
0.8372	Intermediate Similarity	NPC133588
0.8372	Intermediate Similarity	NPC471952
0.8372	Intermediate Similarity	NPC328313
0.8372	Intermediate Similarity	NPC470613
0.8354	Intermediate Similarity	NPC328104
0.8354	Intermediate Similarity	NPC103822
0.8354	Intermediate Similarity	NPC319090
0.8354	Intermediate Similarity	NPC291503
0.8354	Intermediate Similarity	NPC322353
0.8354	Intermediate Similarity	NPC121744
0.8354	Intermediate Similarity	NPC118508
0.8353	Intermediate Similarity	NPC299068
0.8353	Intermediate Similarity	NPC121981
0.8353	Intermediate Similarity	NPC474970
0.8353	Intermediate Similarity	NPC477604
0.8352	Intermediate Similarity	NPC309493
0.8333	Intermediate Similarity	NPC221758
0.8333	Intermediate Similarity	NPC33913
0.8333	Intermediate Similarity	NPC474493
0.8333	Intermediate Similarity	NPC256567
0.8333	Intermediate Similarity	NPC472265
0.8333	Intermediate Similarity	NPC82902
0.8333	Intermediate Similarity	NPC59453
0.8313	Intermediate Similarity	NPC470049
0.8313	Intermediate Similarity	NPC7988
0.8295	Intermediate Similarity	NPC234335
0.8295	Intermediate Similarity	NPC210268
0.8293	Intermediate Similarity	NPC287749
0.8293	Intermediate Similarity	NPC13554

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 NPC1272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1605
0.2-0.3	4452
0.3-0.4	2108
0.4-0.5	391
0.5-0.6	164
0.6-0.7	144
0.7-0.8	113
0.8-0.85	21
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9211	High Similarity	NPD3701	Clinical (unspecified phase)
0.9079	High Similarity	NPD7339	Approved
0.9079	High Similarity	NPD6942	Approved
0.875	High Similarity	NPD7525	Registered
0.869	High Similarity	NPD4751	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4784	Approved
0.8462	Intermediate Similarity	NPD4785	Approved
0.8442	Intermediate Similarity	NPD4243	Approved
0.8333	Intermediate Similarity	NPD4786	Approved
0.8228	Intermediate Similarity	NPD6926	Approved
0.8228	Intermediate Similarity	NPD6924	Approved
0.8171	Intermediate Similarity	NPD6929	Approved
0.8118	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD3667	Approved
0.8072	Intermediate Similarity	NPD6930	Phase 2
0.8072	Intermediate Similarity	NPD6931	Approved
0.8072	Intermediate Similarity	NPD4748	Discontinued
0.8025	Intermediate Similarity	NPD6933	Approved
0.8	Intermediate Similarity	NPD6695	Phase 3
0.7975	Intermediate Similarity	NPD7150	Approved
0.7975	Intermediate Similarity	NPD7152	Approved
0.7975	Intermediate Similarity	NPD7151	Approved
0.7949	Intermediate Similarity	NPD6923	Approved
0.7949	Intermediate Similarity	NPD6922	Approved
0.7927	Intermediate Similarity	NPD6932	Approved
0.7927	Intermediate Similarity	NPD5776	Phase 2
0.7927	Intermediate Similarity	NPD6925	Approved
0.7907	Intermediate Similarity	NPD3133	Approved
0.7907	Intermediate Similarity	NPD3666	Approved
0.7907	Intermediate Similarity	NPD3665	Phase 1
0.7901	Intermediate Similarity	NPD5275	Approved
0.7901	Intermediate Similarity	NPD4190	Phase 3
0.7848	Intermediate Similarity	NPD7143	Approved
0.7848	Intermediate Similarity	NPD7144	Approved
0.7831	Intermediate Similarity	NPD7145	Approved
0.7802	Intermediate Similarity	NPD4202	Approved
0.7802	Intermediate Similarity	NPD6399	Phase 3
0.7738	Intermediate Similarity	NPD7645	Phase 2
0.7738	Intermediate Similarity	NPD4195	Approved
0.7738	Intermediate Similarity	NPD6683	Phase 2
0.7667	Intermediate Similarity	NPD5328	Approved
0.7667	Intermediate Similarity	NPD4753	Phase 2
0.766	Intermediate Similarity	NPD4755	Approved
0.7647	Intermediate Similarity	NPD7509	Discontinued
0.7647	Intermediate Similarity	NPD7514	Phase 3
0.764	Intermediate Similarity	NPD7524	Approved
0.764	Intermediate Similarity	NPD7750	Discontinued
0.7614	Intermediate Similarity	NPD6893	Approved
0.7558	Intermediate Similarity	NPD6902	Approved
0.7528	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.75	Intermediate Similarity	NPD6079	Approved
0.7471	Intermediate Similarity	NPD4221	Approved
0.7471	Intermediate Similarity	NPD4223	Phase 3
0.7442	Intermediate Similarity	NPD7332	Phase 2
0.7423	Intermediate Similarity	NPD5223	Approved
0.7416	Intermediate Similarity	NPD5329	Approved
0.7396	Intermediate Similarity	NPD7638	Approved
0.7356	Intermediate Similarity	NPD6898	Phase 1
0.7347	Intermediate Similarity	NPD4633	Approved
0.7347	Intermediate Similarity	NPD5226	Approved
0.7347	Intermediate Similarity	NPD5224	Approved
0.7347	Intermediate Similarity	NPD5211	Phase 2
0.7347	Intermediate Similarity	NPD5225	Approved
0.732	Intermediate Similarity	NPD7639	Approved
0.732	Intermediate Similarity	NPD7640	Approved
0.7312	Intermediate Similarity	NPD7087	Discontinued
0.7303	Intermediate Similarity	NPD4197	Approved
0.73	Intermediate Similarity	NPD5739	Approved
0.73	Intermediate Similarity	NPD7128	Approved
0.73	Intermediate Similarity	NPD6675	Approved
0.73	Intermediate Similarity	NPD6402	Approved
0.7292	Intermediate Similarity	NPD6083	Phase 2
0.7292	Intermediate Similarity	NPD6084	Phase 2
0.7283	Intermediate Similarity	NPD6051	Approved
0.7273	Intermediate Similarity	NPD5175	Approved
0.7273	Intermediate Similarity	NPD5174	Approved
0.7273	Intermediate Similarity	NPD4754	Approved
0.7263	Intermediate Similarity	NPD5210	Approved
0.7263	Intermediate Similarity	NPD4629	Approved
0.7228	Intermediate Similarity	NPD6412	Phase 2
0.7209	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5141	Approved
0.7191	Intermediate Similarity	NPD4788	Approved
0.7188	Intermediate Similarity	NPD4697	Phase 3
0.7188	Intermediate Similarity	NPD5221	Approved
0.7188	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5222	Approved
0.7184	Intermediate Similarity	NPD4634	Approved
0.7157	Intermediate Similarity	NPD6881	Approved
0.7157	Intermediate Similarity	NPD6899	Approved
0.7157	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD4689	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD4693	Phase 3
0.7143	Intermediate Similarity	NPD4690	Approved
0.7143	Intermediate Similarity	NPD5205	Approved
0.7143	Intermediate Similarity	NPD4138	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD4688	Approved
0.7129	Intermediate Similarity	NPD4767	Approved
0.7129	Intermediate Similarity	NPD4768	Approved
0.7113	Intermediate Similarity	NPD5173	Approved
0.7087	Intermediate Similarity	NPD6372	Approved
0.7087	Intermediate Similarity	NPD6373	Approved
0.7059	Intermediate Similarity	NPD5701	Approved
0.7059	Intermediate Similarity	NPD5697	Approved
0.7059	Intermediate Similarity	NPD8264	Approved
0.7033	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7290	Approved
0.7019	Intermediate Similarity	NPD7102	Approved
0.7019	Intermediate Similarity	NPD6883	Approved
0.699	Remote Similarity	NPD4729	Approved
0.699	Remote Similarity	NPD6011	Approved
0.699	Remote Similarity	NPD5128	Approved
0.699	Remote Similarity	NPD4730	Approved
0.6989	Remote Similarity	NPD4722	Approved
0.6989	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4723	Approved
0.6989	Remote Similarity	NPD6903	Approved
0.6988	Remote Similarity	NPD4787	Phase 1
0.6981	Remote Similarity	NPD4632	Approved
0.6961	Remote Similarity	NPD6008	Approved
0.6957	Remote Similarity	NPD5280	Approved
0.6957	Remote Similarity	NPD5690	Phase 2
0.6957	Remote Similarity	NPD4694	Approved
0.6952	Remote Similarity	NPD6650	Approved
0.6952	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD8130	Phase 1
0.6952	Remote Similarity	NPD6617	Approved
0.6952	Remote Similarity	NPD6869	Approved
0.6952	Remote Similarity	NPD6649	Approved
0.6952	Remote Similarity	NPD6847	Approved
0.6947	Remote Similarity	NPD7637	Suspended
0.6947	Remote Similarity	NPD5281	Approved
0.6947	Remote Similarity	NPD5284	Approved
0.6947	Remote Similarity	NPD7515	Phase 2
0.6923	Remote Similarity	NPD6012	Approved
0.6923	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6013	Approved
0.6907	Remote Similarity	NPD5695	Phase 3
0.6887	Remote Similarity	NPD8297	Approved
0.6887	Remote Similarity	NPD6882	Approved
0.6869	Remote Similarity	NPD5696	Approved
0.6867	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5247	Approved
0.6857	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5135	Approved
0.6857	Remote Similarity	NPD5169	Approved
0.6857	Remote Similarity	NPD5249	Phase 3
0.6857	Remote Similarity	NPD5248	Approved
0.6857	Remote Similarity	NPD5250	Approved
0.6857	Remote Similarity	NPD5251	Approved
0.6854	Remote Similarity	NPD6928	Phase 2
0.6842	Remote Similarity	NPD7136	Phase 2
0.6809	Remote Similarity	NPD6672	Approved
0.6809	Remote Similarity	NPD5737	Approved
0.6792	Remote Similarity	NPD5127	Approved
0.6792	Remote Similarity	NPD5215	Approved
0.6792	Remote Similarity	NPD5217	Approved
0.6792	Remote Similarity	NPD5216	Approved
0.6789	Remote Similarity	NPD6009	Approved
0.6778	Remote Similarity	NPD4139	Approved
0.6778	Remote Similarity	NPD4692	Approved
0.6774	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6098	Approved
0.6771	Remote Similarity	NPD8035	Phase 2
0.6771	Remote Similarity	NPD8034	Phase 2
0.6757	Remote Similarity	NPD6059	Approved
0.6757	Remote Similarity	NPD6054	Approved
0.6737	Remote Similarity	NPD6904	Approved
0.6737	Remote Similarity	NPD6673	Approved
0.6737	Remote Similarity	NPD6080	Approved
0.6727	Remote Similarity	NPD7327	Approved
0.6727	Remote Similarity	NPD7328	Approved
0.67	Remote Similarity	NPD5290	Discontinued
0.6696	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD7632	Discontinued
0.6637	Remote Similarity	NPD6370	Approved
0.6633	Remote Similarity	NPD7748	Approved
0.6629	Remote Similarity	NPD6697	Approved
0.6629	Remote Similarity	NPD3617	Approved
0.6629	Remote Similarity	NPD6118	Approved
0.6629	Remote Similarity	NPD6115	Approved
0.6629	Remote Similarity	NPD6114	Approved
0.6607	Remote Similarity	NPD8377	Approved
0.6607	Remote Similarity	NPD8294	Approved
0.6607	Remote Similarity	NPD6319	Approved
0.6606	Remote Similarity	NPD5167	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