NPASS Compound

Structure

NPC246445 OpenBabel07101719252D 34 37 0 0 1 0 0 0 0 0999 V2000 4.7090 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1051 1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3564 2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0281 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 3.1470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3301 2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7566 0.7401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -0.1860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1304 3.1470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1337 -2.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6173 2.3038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6173 3.9902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1653 -2.4518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7060 -3.1378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 19 21 1 0 0 0 0 20 18 1 6 0 0 0 20 25 1 0 0 0 0 21 27 1 1 0 0 0 22 25 1 0 0 0 0 22 28 1 6 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 31 2 0 0 0 0 24 32 1 0 0 0 0 25 30 1 1 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	6.272
LogD:	5.323
LogS:	-4.388
# Rotatable Bonds:	6
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.394
Synthetic Accessibility Score:	4.737
Fsp3:	0.867
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:	-5.693
MDCK Permeability:	5.599815267487429e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	95.29926300048828%
Volume Distribution (VD):	0.556
Pgp-substrate:	2.7750444412231445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.451
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	1.684
Half-life (T1/2):	0.518

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.434
Drug-inuced Liver Injury (DILI):	0.009
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.315
Carcinogencity:	0.058
Eye Corrosion:	0.198
Eye Irritation:	0.099
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC246445

Natural Product ID:	NPC246445
*Common Name:**	3,4-Seco-Lupan-20(30)-Ene-3,28-Dioic Acid
IUPAC Name:	(3S,4S,5R,8R,9R,10R,13S,14R,15R)-4-(2-carboxyethyl)-4,9,10-trimethyl-3-propan-2-yl-15-prop-1-en-2-yl-2,3,5,6,7,8,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid
Synonyms:
Standard InCHIKey:	WIPYWDLXFRPWFA-RGAAFHQASA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-18(2)20-10-15-30(26(33)34)17-16-28(6)22(25(20)30)8-9-23-27(5,13-12-24(31)32)21(19(3)4)11-14-29(23,28)7/h19-23,25H,1,8-17H2,2-7H3,(H,31,32)(H,33,34)/t20-,21-,22+,23+,25+,27-,28+,29+,30-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@](C)(CCC(=O)O)[C@@H](CC[C@@]34C)C(C)C)[C@@H]12)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063163
PubChem CID:	70682277
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003364] Steroid acids [CHEMONTID:0003368] 3-carboxy steroids

*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
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	Fruits	n.a.	n.a.	PMID[22691179]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	10000.0	nM	PMID[548531]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[548531]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	<	10000.0	nM	PMID[548531]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[548531]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[548531]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	<	10000.0	nM	PMID[548531]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	IC50	<	10000.0	nM	PMID[548531]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[548531]

☑ 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 NPC246445 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	149
0.1-0.2	1599
0.2-0.3	9558
0.3-0.4	14202
0.4-0.5	6020
0.5-0.6	5988
0.6-0.7	3666
0.7-0.8	1322
0.8-0.85	138
0.85-0.9	40
0.9-0.95	9
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC66105
0.9583	High Similarity	NPC68828
0.9571	High Similarity	NPC244708
0.9571	High Similarity	NPC330659
0.9571	High Similarity	NPC161187
0.9324	High Similarity	NPC192744
0.9091	High Similarity	NPC167103
0.9054	High Similarity	NPC471035
0.9054	High Similarity	NPC212661
0.9028	High Similarity	NPC36310
0.9028	High Similarity	NPC279241
0.9	High Similarity	NPC290445
0.9	High Similarity	NPC36616
0.8933	High Similarity	NPC321690
0.8919	High Similarity	NPC20466
0.8861	High Similarity	NPC201655
0.8846	High Similarity	NPC471037
0.8846	High Similarity	NPC472740
0.8846	High Similarity	NPC245866
0.8831	High Similarity	NPC232625
0.8831	High Similarity	NPC147066
0.8816	High Similarity	NPC158846
0.88	High Similarity	NPC238227
0.875	High Similarity	NPC70661
0.875	High Similarity	NPC2783
0.875	High Similarity	NPC80590
0.8714	High Similarity	NPC477931
0.8714	High Similarity	NPC42060
0.8714	High Similarity	NPC268736
0.8684	High Similarity	NPC280654
0.8684	High Similarity	NPC260385
0.8684	High Similarity	NPC110094
0.8684	High Similarity	NPC63020
0.8667	High Similarity	NPC89294
0.8649	High Similarity	NPC255168
0.8642	High Similarity	NPC264005
0.8642	High Similarity	NPC269360
0.8642	High Similarity	NPC33768
0.8642	High Similarity	NPC134197
0.8625	High Similarity	NPC294438
0.8625	High Similarity	NPC264317
0.859	High Similarity	NPC38350
0.859	High Similarity	NPC201912
0.8571	High Similarity	NPC201459
0.8571	High Similarity	NPC199595
0.8571	High Similarity	NPC215843
0.8571	High Similarity	NPC477371
0.8553	High Similarity	NPC471897
0.8553	High Similarity	NPC471899
0.8553	High Similarity	NPC107039
0.8537	High Similarity	NPC4309
0.8537	High Similarity	NPC183374
0.8537	High Similarity	NPC211162
0.8537	High Similarity	NPC474719
0.8537	High Similarity	NPC16377
0.8519	High Similarity	NPC472505
0.8519	High Similarity	NPC12774
0.85	High Similarity	NPC263974
0.8493	Intermediate Similarity	NPC91369
0.8481	Intermediate Similarity	NPC260956
0.8481	Intermediate Similarity	NPC320514
0.8481	Intermediate Similarity	NPC133391
0.8481	Intermediate Similarity	NPC170985
0.8462	Intermediate Similarity	NPC37038
0.8462	Intermediate Similarity	NPC104545
0.8434	Intermediate Similarity	NPC24772
0.8434	Intermediate Similarity	NPC213832
0.8434	Intermediate Similarity	NPC116146
0.8434	Intermediate Similarity	NPC220498
0.8434	Intermediate Similarity	NPC247312
0.8434	Intermediate Similarity	NPC57954
0.8434	Intermediate Similarity	NPC271974
0.8415	Intermediate Similarity	NPC96496
0.8415	Intermediate Similarity	NPC136948
0.8395	Intermediate Similarity	NPC29447
0.8395	Intermediate Similarity	NPC269638
0.8378	Intermediate Similarity	NPC72343
0.8378	Intermediate Similarity	NPC469940
0.8375	Intermediate Similarity	NPC83569
0.8375	Intermediate Similarity	NPC477373
0.8375	Intermediate Similarity	NPC470015
0.8375	Intermediate Similarity	NPC168188
0.8375	Intermediate Similarity	NPC69279
0.8356	Intermediate Similarity	NPC469941
0.8356	Intermediate Similarity	NPC252032
0.8356	Intermediate Similarity	NPC476734
0.8356	Intermediate Similarity	NPC319671
0.8354	Intermediate Similarity	NPC221647
0.8354	Intermediate Similarity	NPC477372
0.8354	Intermediate Similarity	NPC103754
0.8354	Intermediate Similarity	NPC474484
0.8333	Intermediate Similarity	NPC196827
0.8333	Intermediate Similarity	NPC471475
0.8333	Intermediate Similarity	NPC274996
0.8333	Intermediate Similarity	NPC231431
0.8333	Intermediate Similarity	NPC169933
0.8333	Intermediate Similarity	NPC474221
0.8333	Intermediate Similarity	NPC130459
0.8333	Intermediate Similarity	NPC16394
0.8333	Intermediate Similarity	NPC478180
0.8333	Intermediate Similarity	NPC118987
0.8313	Intermediate Similarity	NPC255176
0.8313	Intermediate Similarity	NPC146937
0.8313	Intermediate Similarity	NPC471900
0.8312	Intermediate Similarity	NPC106078
0.8293	Intermediate Similarity	NPC186975
0.8293	Intermediate Similarity	NPC475007
0.8293	Intermediate Similarity	NPC155011
0.8289	Intermediate Similarity	NPC192540
0.8289	Intermediate Similarity	NPC201027
0.8289	Intermediate Similarity	NPC279666
0.8272	Intermediate Similarity	NPC476038
0.8272	Intermediate Similarity	NPC248758
0.8272	Intermediate Similarity	NPC19849
0.8272	Intermediate Similarity	NPC194937
0.8272	Intermediate Similarity	NPC164577
0.8272	Intermediate Similarity	NPC472864
0.825	Intermediate Similarity	NPC145143
0.825	Intermediate Similarity	NPC477858
0.8243	Intermediate Similarity	NPC235586
0.8243	Intermediate Similarity	NPC477929
0.8243	Intermediate Similarity	NPC108131
0.8235	Intermediate Similarity	NPC471901
0.8235	Intermediate Similarity	NPC160506
0.8228	Intermediate Similarity	NPC477057
0.8228	Intermediate Similarity	NPC170038
0.8214	Intermediate Similarity	NPC475921
0.8214	Intermediate Similarity	NPC262043
0.8214	Intermediate Similarity	NPC474570
0.8214	Intermediate Similarity	NPC474704
0.8205	Intermediate Similarity	NPC476810
0.8193	Intermediate Similarity	NPC474684
0.8193	Intermediate Similarity	NPC142361
0.8193	Intermediate Similarity	NPC236618
0.8193	Intermediate Similarity	NPC128644
0.8182	Intermediate Similarity	NPC104806
0.8182	Intermediate Similarity	NPC69143
0.8182	Intermediate Similarity	NPC476601
0.8171	Intermediate Similarity	NPC283733
0.8171	Intermediate Similarity	NPC98270
0.8171	Intermediate Similarity	NPC123319
0.8171	Intermediate Similarity	NPC94531
0.8171	Intermediate Similarity	NPC311702
0.8158	Intermediate Similarity	NPC103958
0.8158	Intermediate Similarity	NPC18819
0.8158	Intermediate Similarity	NPC251970
0.8158	Intermediate Similarity	NPC477930
0.8158	Intermediate Similarity	NPC183503
0.8158	Intermediate Similarity	NPC161923
0.8158	Intermediate Similarity	NPC283908
0.8158	Intermediate Similarity	NPC241854
0.8158	Intermediate Similarity	NPC476046
0.8158	Intermediate Similarity	NPC46610
0.8148	Intermediate Similarity	NPC175410
0.8148	Intermediate Similarity	NPC215893
0.8148	Intermediate Similarity	NPC477852
0.8148	Intermediate Similarity	NPC170862
0.8148	Intermediate Similarity	NPC97913
0.8148	Intermediate Similarity	NPC475726
0.8148	Intermediate Similarity	NPC200752
0.8148	Intermediate Similarity	NPC472743
0.814	Intermediate Similarity	NPC473690
0.814	Intermediate Similarity	NPC287118
0.814	Intermediate Similarity	NPC475061
0.814	Intermediate Similarity	NPC224060
0.814	Intermediate Similarity	NPC471902
0.814	Intermediate Similarity	NPC291373
0.814	Intermediate Similarity	NPC244356
0.8133	Intermediate Similarity	NPC160817
0.8125	Intermediate Similarity	NPC142244
0.8125	Intermediate Similarity	NPC471898
0.8125	Intermediate Similarity	NPC278459
0.8125	Intermediate Similarity	NPC263272
0.8125	Intermediate Similarity	NPC267691
0.8125	Intermediate Similarity	NPC274050
0.8125	Intermediate Similarity	NPC162632
0.8118	Intermediate Similarity	NPC471896
0.8108	Intermediate Similarity	NPC474962
0.8108	Intermediate Similarity	NPC64466
0.8108	Intermediate Similarity	NPC196197
0.8095	Intermediate Similarity	NPC48824
0.8095	Intermediate Similarity	NPC229407
0.8095	Intermediate Similarity	NPC117122
0.8095	Intermediate Similarity	NPC254572
0.8095	Intermediate Similarity	NPC250687
0.8095	Intermediate Similarity	NPC242864
0.8072	Intermediate Similarity	NPC472869
0.8072	Intermediate Similarity	NPC55309
0.8072	Intermediate Similarity	NPC28252
0.8052	Intermediate Similarity	NPC476844
0.8052	Intermediate Similarity	NPC477934
0.8049	Intermediate Similarity	NPC472865
0.8049	Intermediate Similarity	NPC475745
0.8049	Intermediate Similarity	NPC74595
0.8049	Intermediate Similarity	NPC474233
0.8049	Intermediate Similarity	NPC475509
0.8049	Intermediate Similarity	NPC156981
0.8049	Intermediate Similarity	NPC165064
0.8049	Intermediate Similarity	NPC96095
0.8049	Intermediate Similarity	NPC264665

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 NPC246445 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	2061
0.2-0.3	4269
0.3-0.4	1782
0.4-0.5	462
0.5-0.6	181
0.6-0.7	165
0.7-0.8	82
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8625	High Similarity	NPD7520	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD6081	Approved
0.8235	Intermediate Similarity	NPD8034	Phase 2
0.8235	Intermediate Similarity	NPD8035	Phase 2
0.8194	Intermediate Similarity	NPD4224	Phase 2
0.8148	Intermediate Similarity	NPD4788	Approved
0.7949	Intermediate Similarity	NPD6117	Approved
0.7931	Intermediate Similarity	NPD6399	Phase 3
0.7922	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6116	Phase 1
0.7831	Intermediate Similarity	NPD4786	Approved
0.7805	Intermediate Similarity	NPD4223	Phase 3
0.7805	Intermediate Similarity	NPD4221	Approved
0.775	Intermediate Similarity	NPD6697	Approved
0.775	Intermediate Similarity	NPD6118	Approved
0.775	Intermediate Similarity	NPD6115	Approved
0.775	Intermediate Similarity	NPD6114	Approved
0.7738	Intermediate Similarity	NPD5329	Approved
0.7733	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5360	Phase 3
0.7674	Intermediate Similarity	NPD6672	Approved
0.7674	Intermediate Similarity	NPD5737	Approved
0.7647	Intermediate Similarity	NPD6098	Approved
0.7619	Intermediate Similarity	NPD4197	Approved
0.7614	Intermediate Similarity	NPD5284	Approved
0.7614	Intermediate Similarity	NPD5281	Approved
0.759	Intermediate Similarity	NPD3667	Approved
0.7586	Intermediate Similarity	NPD6673	Approved
0.7586	Intermediate Similarity	NPD6080	Approved
0.7586	Intermediate Similarity	NPD6904	Approved
0.7582	Intermediate Similarity	NPD6084	Phase 2
0.7582	Intermediate Similarity	NPD6083	Phase 2
0.7532	Intermediate Similarity	NPD4789	Approved
0.7531	Intermediate Similarity	NPD3617	Approved
0.7471	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6684	Approved
0.7442	Intermediate Similarity	NPD4690	Approved
0.7442	Intermediate Similarity	NPD4693	Phase 3
0.7442	Intermediate Similarity	NPD7334	Approved
0.7442	Intermediate Similarity	NPD7521	Approved
0.7442	Intermediate Similarity	NPD4688	Approved
0.7442	Intermediate Similarity	NPD7146	Approved
0.7442	Intermediate Similarity	NPD5205	Approved
0.7442	Intermediate Similarity	NPD6409	Approved
0.7442	Intermediate Similarity	NPD4138	Approved
0.7442	Intermediate Similarity	NPD5330	Approved
0.7442	Intermediate Similarity	NPD4689	Approved
0.7436	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7515	Phase 2
0.7412	Intermediate Similarity	NPD3666	Approved
0.7412	Intermediate Similarity	NPD3665	Phase 1
0.7412	Intermediate Similarity	NPD3133	Approved
0.7386	Intermediate Similarity	NPD5328	Approved
0.7386	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4753	Phase 2
0.7375	Intermediate Similarity	NPD3702	Approved
0.7363	Intermediate Similarity	NPD5695	Phase 3
0.7333	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5696	Approved
0.7308	Intermediate Similarity	NPD4244	Approved
0.7308	Intermediate Similarity	NPD4245	Approved
0.7273	Intermediate Similarity	NPD5208	Approved
0.7273	Intermediate Similarity	NPD6903	Approved
0.7262	Intermediate Similarity	NPD4692	Approved
0.7262	Intermediate Similarity	NPD4139	Approved
0.7253	Intermediate Similarity	NPD7748	Approved
0.7241	Intermediate Similarity	NPD5280	Approved
0.7241	Intermediate Similarity	NPD4694	Approved
0.7241	Intermediate Similarity	NPD3618	Phase 1
0.7241	Intermediate Similarity	NPD5690	Phase 2
0.7241	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5693	Phase 1
0.7222	Intermediate Similarity	NPD6050	Approved
0.7222	Intermediate Similarity	NPD6079	Approved
0.7215	Intermediate Similarity	NPD5777	Approved
0.7215	Intermediate Similarity	NPD4243	Approved
0.7215	Intermediate Similarity	NPD4758	Discontinued
0.7209	Intermediate Similarity	NPD3668	Phase 3
0.7179	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3698	Phase 2
0.7179	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.7143	Intermediate Similarity	NPD7525	Registered
0.7128	Intermediate Similarity	NPD7638	Approved
0.7111	Intermediate Similarity	NPD5692	Phase 3
0.7108	Intermediate Similarity	NPD5364	Discontinued
0.7089	Intermediate Similarity	NPD4747	Approved
0.7053	Intermediate Similarity	NPD7640	Approved
0.7053	Intermediate Similarity	NPD6404	Discontinued
0.7053	Intermediate Similarity	NPD7639	Approved
0.7045	Intermediate Similarity	NPD5279	Phase 3
0.7041	Intermediate Similarity	NPD6675	Approved
0.7041	Intermediate Similarity	NPD6402	Approved
0.7041	Intermediate Similarity	NPD7128	Approved
0.7041	Intermediate Similarity	NPD5739	Approved
0.7037	Intermediate Similarity	NPD4784	Approved
0.7037	Intermediate Similarity	NPD4785	Approved
0.7033	Intermediate Similarity	NPD5694	Approved
0.7024	Intermediate Similarity	NPD4195	Approved
0.7021	Intermediate Similarity	NPD7902	Approved
0.6989	Remote Similarity	NPD4629	Approved
0.6989	Remote Similarity	NPD5210	Approved
0.6977	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4137	Phase 3
0.6957	Remote Similarity	NPD4202	Approved
0.6951	Remote Similarity	NPD6942	Approved
0.6951	Remote Similarity	NPD7339	Approved
0.6923	Remote Similarity	NPD5207	Approved
0.6915	Remote Similarity	NPD4697	Phase 3
0.6915	Remote Similarity	NPD5221	Approved
0.6915	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5222	Approved
0.6915	Remote Similarity	NPD7614	Phase 1
0.6905	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7320	Approved
0.69	Remote Similarity	NPD6881	Approved
0.69	Remote Similarity	NPD6899	Approved
0.6882	Remote Similarity	NPD6001	Approved
0.6875	Remote Similarity	NPD4691	Approved
0.6854	Remote Similarity	NPD4519	Discontinued
0.6854	Remote Similarity	NPD4623	Approved
0.6842	Remote Similarity	NPD5173	Approved
0.6842	Remote Similarity	NPD4755	Approved
0.6835	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6373	Approved
0.6832	Remote Similarity	NPD6372	Approved
0.6829	Remote Similarity	NPD5733	Approved
0.68	Remote Similarity	NPD5697	Approved
0.68	Remote Similarity	NPD5701	Approved
0.6765	Remote Similarity	NPD7102	Approved
0.6765	Remote Similarity	NPD7290	Approved
0.6765	Remote Similarity	NPD6883	Approved
0.6747	Remote Similarity	NPD3703	Phase 2
0.6747	Remote Similarity	NPD4190	Phase 3
0.6747	Remote Similarity	NPD5275	Approved
0.6739	Remote Similarity	NPD4096	Approved
0.6733	Remote Similarity	NPD6011	Approved
0.6702	Remote Similarity	NPD7900	Approved
0.6702	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5285	Approved
0.6701	Remote Similarity	NPD5286	Approved
0.6701	Remote Similarity	NPD4700	Approved
0.6701	Remote Similarity	NPD4696	Approved
0.6699	Remote Similarity	NPD6847	Approved
0.6699	Remote Similarity	NPD6650	Approved
0.6699	Remote Similarity	NPD6617	Approved
0.6699	Remote Similarity	NPD6869	Approved
0.6699	Remote Similarity	NPD6649	Approved
0.6699	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6052	Approved
0.6635	Remote Similarity	NPD6882	Approved
0.6635	Remote Similarity	NPD8297	Approved
0.6633	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD5654	Approved
0.663	Remote Similarity	NPD6051	Approved
0.6627	Remote Similarity	NPD6924	Approved
0.6627	Remote Similarity	NPD6926	Approved
0.6627	Remote Similarity	NPD4687	Approved
0.6627	Remote Similarity	NPD4058	Approved
0.6596	Remote Similarity	NPD5133	Approved
0.6593	Remote Similarity	NPD3573	Approved
0.6585	Remote Similarity	NPD5276	Approved
0.6571	Remote Similarity	NPD8133	Approved
0.6566	Remote Similarity	NPD5224	Approved
0.6566	Remote Similarity	NPD5211	Phase 2
0.6566	Remote Similarity	NPD4633	Approved
0.6566	Remote Similarity	NPD5091	Approved
0.6566	Remote Similarity	NPD5226	Approved
0.6566	Remote Similarity	NPD7632	Discontinued
0.6566	Remote Similarity	NPD5225	Approved
0.6522	Remote Similarity	NPD4518	Approved
0.6517	Remote Similarity	NPD5362	Discontinued
0.6512	Remote Similarity	NPD3671	Phase 1
0.65	Remote Similarity	NPD4754	Approved
0.65	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD5175	Approved
0.6495	Remote Similarity	NPD5959	Approved
0.6489	Remote Similarity	NPD7637	Suspended
0.6489	Remote Similarity	NPD6411	Approved
0.6471	Remote Similarity	NPD6412	Phase 2
0.6471	Remote Similarity	NPD6614	Approved
0.6471	Remote Similarity	NPD6933	Approved
0.6449	Remote Similarity	NPD6868	Approved
0.6436	Remote Similarity	NPD5141	Approved
0.6415	Remote Similarity	NPD4632	Approved
0.6392	Remote Similarity	NPD7732	Phase 3
0.6389	Remote Similarity	NPD7115	Discovery
0.6373	Remote Similarity	NPD4768	Approved
0.6373	Remote Similarity	NPD4767	Approved
0.6373	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD5368	Approved
0.6341	Remote Similarity	NPD6923	Approved
0.6341	Remote Similarity	NPD6922	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