NPASS Compound

Structure

NPC36310 OpenBabel07101718222D 32 35 0 0 1 0 0 0 0 0999 V2000 -3.3679 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 -2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3281 -2.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -3.1423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3559 -2.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6839 -0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6839 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3559 -3.9842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5259 1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8420 -1.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8420 0.4861 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 -0.8420 -4.8262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6164 -3.9842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 21 4 1 6 0 0 0 21 26 1 0 0 0 0 22 28 1 6 0 0 0 23 26 1 0 0 0 0 23 29 1 1 0 0 0 24 28 1 6 0 0 0 24 30 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 27 1 1 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	502.881
LogP:	6.964
LogD:	5.273
LogS:	-6.078
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	4.953
Fsp3:	0.833
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:	-5.23
MDCK Permeability:	1.170810719486326e-05
Pgp-inhibitor:	0.113
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.819
30% Bioavailability (F30%):	0.16

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	96.0700454711914%
Volume Distribution (VD):	0.678
Pgp-substrate:	2.842154026031494%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.435
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.171
CYP2C9-substrate:	0.687
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.315
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	3.11
Half-life (T1/2):	0.24

ADMET: Toxicity

hERG Blockers:	0.176
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.126
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.429
Carcinogencity:	0.044
Eye Corrosion:	0.587
Eye Irritation:	0.239
Respiratory Toxicity:	0.584

Download Data

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

Natural Product: NPC36310

Natural Product ID:	NPC36310
*Common Name:**	3,4-Seco-Urs-4(23),20(30)-Dien-3-Oic Acid
IUPAC Name:	3-[(1S,2S,4aR,4bR,6aR,10R,10aS,10bR,12aR)-1,4a,4b,6a,10-pentamethyl-9-methylidene-2-prop-1-en-2-yl-3,4,5,6,7,8,10,10a,10b,11,12,12a-dodecahydro-2H-chrysen-1-yl]propanoic acid
Synonyms:
Standard InCHIKey:	KAKDSTYYULDNHW-MHISZOMXSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-19(2)22-12-16-30(8)24(28(22,6)15-13-25(31)32)10-9-23-26-21(4)20(3)11-14-27(26,5)17-18-29(23,30)7/h21-24,26H,1,3,9-18H2,2,4-8H3,(H,31,32)/t21-,22-,23+,24+,26-,27+,28-,29+,30+/m0/s1
SMILES:	OC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@]2([C@H]1[C@@H](C)C(=C)CC2)C)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375731
PubChem CID:	16215549
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003364] Steroid acids

*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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100000.0	nM	PMID[515085]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[515085]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[515085]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	>	100000.0	nM	PMID[515085]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[515085]

☑ 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 NPC36310 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	187
0.1-0.2	1884
0.2-0.3	10122
0.3-0.4	14398
0.4-0.5	6846
0.5-0.6	5533
0.6-0.7	2780
0.7-0.8	751
0.8-0.85	158
0.85-0.9	33
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC255168
0.9437	High Similarity	NPC68828
0.9296	High Similarity	NPC89294
0.9178	High Similarity	NPC16394
0.9178	High Similarity	NPC192744
0.9167	High Similarity	NPC107039
0.9167	High Similarity	NPC471897
0.9167	High Similarity	NPC471899
0.9143	High Similarity	NPC330659
0.9143	High Similarity	NPC244708
0.9143	High Similarity	NPC161187
0.9118	High Similarity	NPC290445
0.9118	High Similarity	NPC36616
0.9041	High Similarity	NPC260385
0.9041	High Similarity	NPC110094
0.9041	High Similarity	NPC280654
0.9028	High Similarity	NPC246445
0.8933	High Similarity	NPC267691
0.8933	High Similarity	NPC274050
0.8933	High Similarity	NPC162632
0.8933	High Similarity	NPC263272
0.8919	High Similarity	NPC231431
0.8919	High Similarity	NPC199595
0.8904	High Similarity	NPC66105
0.8857	High Similarity	NPC91369
0.8816	High Similarity	NPC69101
0.8816	High Similarity	NPC251779
0.88	High Similarity	NPC37038
0.88	High Similarity	NPC104545
0.8732	High Similarity	NPC72343
0.8701	High Similarity	NPC200752
0.8701	High Similarity	NPC70834
0.8701	High Similarity	NPC472740
0.8684	High Similarity	NPC142244
0.8684	High Similarity	NPC471898
0.8684	High Similarity	NPC221647
0.8649	High Similarity	NPC471035
0.8649	High Similarity	NPC212661
0.863	High Similarity	NPC279666
0.863	High Similarity	NPC192540
0.8611	High Similarity	NPC279241
0.8592	High Similarity	NPC235586
0.859	High Similarity	NPC96095
0.8553	High Similarity	NPC477057
0.8533	High Similarity	NPC63020
0.8514	High Similarity	NPC69143
0.8514	High Similarity	NPC104806
0.8514	High Similarity	NPC20466
0.8493	Intermediate Similarity	NPC476046
0.8493	Intermediate Similarity	NPC251970
0.8493	Intermediate Similarity	NPC183503
0.8493	Intermediate Similarity	NPC18819
0.8493	Intermediate Similarity	NPC46610
0.8493	Intermediate Similarity	NPC103958
0.8493	Intermediate Similarity	NPC241854
0.8493	Intermediate Similarity	NPC161923
0.8493	Intermediate Similarity	NPC283908
0.8481	Intermediate Similarity	NPC201655
0.8481	Intermediate Similarity	NPC294438
0.8481	Intermediate Similarity	NPC264317
0.8472	Intermediate Similarity	NPC160817
0.8421	Intermediate Similarity	NPC201459
0.8378	Intermediate Similarity	NPC476844
0.8378	Intermediate Similarity	NPC201027
0.8375	Intermediate Similarity	NPC187545
0.8375	Intermediate Similarity	NPC12774
0.8375	Intermediate Similarity	NPC2783
0.8354	Intermediate Similarity	NPC156981
0.8354	Intermediate Similarity	NPC477289
0.8312	Intermediate Similarity	NPC267517
0.831	Intermediate Similarity	NPC281203
0.831	Intermediate Similarity	NPC469724
0.831	Intermediate Similarity	NPC31187
0.831	Intermediate Similarity	NPC100917
0.8289	Intermediate Similarity	NPC476810
0.8289	Intermediate Similarity	NPC321690
0.8286	Intermediate Similarity	NPC103734
0.8272	Intermediate Similarity	NPC18064
0.8272	Intermediate Similarity	NPC173089
0.8272	Intermediate Similarity	NPC98442
0.8272	Intermediate Similarity	NPC130577
0.8272	Intermediate Similarity	NPC102683
0.8272	Intermediate Similarity	NPC158141
0.8272	Intermediate Similarity	NPC88716
0.8272	Intermediate Similarity	NPC307426
0.8272	Intermediate Similarity	NPC68160
0.8272	Intermediate Similarity	NPC242468
0.8272	Intermediate Similarity	NPC171203
0.8272	Intermediate Similarity	NPC51700
0.8272	Intermediate Similarity	NPC142415
0.8272	Intermediate Similarity	NPC269360
0.8272	Intermediate Similarity	NPC33768
0.8272	Intermediate Similarity	NPC264005
0.8272	Intermediate Similarity	NPC293564
0.8267	Intermediate Similarity	NPC309399
0.8267	Intermediate Similarity	NPC476601
0.825	Intermediate Similarity	NPC474537
0.8243	Intermediate Similarity	NPC237591
0.8243	Intermediate Similarity	NPC3753
0.8228	Intermediate Similarity	NPC167103
0.8228	Intermediate Similarity	NPC471037
0.8228	Intermediate Similarity	NPC245866
0.8205	Intermediate Similarity	NPC103754
0.8205	Intermediate Similarity	NPC474484
0.8205	Intermediate Similarity	NPC278459
0.8205	Intermediate Similarity	NPC3915
0.8205	Intermediate Similarity	NPC147066
0.8182	Intermediate Similarity	NPC158846
0.8171	Intermediate Similarity	NPC246708
0.8171	Intermediate Similarity	NPC40552
0.8171	Intermediate Similarity	NPC1753
0.8171	Intermediate Similarity	NPC4309
0.8171	Intermediate Similarity	NPC474719
0.8171	Intermediate Similarity	NPC470629
0.8171	Intermediate Similarity	NPC471900
0.8171	Intermediate Similarity	NPC290690
0.8171	Intermediate Similarity	NPC474474
0.8171	Intermediate Similarity	NPC182797
0.8171	Intermediate Similarity	NPC474512
0.8171	Intermediate Similarity	NPC17733
0.8171	Intermediate Similarity	NPC474511
0.8171	Intermediate Similarity	NPC181225
0.8171	Intermediate Similarity	NPC52169
0.8171	Intermediate Similarity	NPC473242
0.8171	Intermediate Similarity	NPC16377
0.8158	Intermediate Similarity	NPC238227
0.8158	Intermediate Similarity	NPC165711
0.8148	Intermediate Similarity	NPC72638
0.8148	Intermediate Similarity	NPC324063
0.8133	Intermediate Similarity	NPC39362
0.8125	Intermediate Similarity	NPC263974
0.8108	Intermediate Similarity	NPC177826
0.8108	Intermediate Similarity	NPC472813
0.8101	Intermediate Similarity	NPC476292
0.8101	Intermediate Similarity	NPC474605
0.8101	Intermediate Similarity	NPC310989
0.8101	Intermediate Similarity	NPC170985
0.8082	Intermediate Similarity	NPC108131
0.8072	Intermediate Similarity	NPC25906
0.8072	Intermediate Similarity	NPC59263
0.8072	Intermediate Similarity	NPC57954
0.8072	Intermediate Similarity	NPC61543
0.8072	Intermediate Similarity	NPC143232
0.8072	Intermediate Similarity	NPC198664
0.8072	Intermediate Similarity	NPC293048
0.8072	Intermediate Similarity	NPC225585
0.8072	Intermediate Similarity	NPC247312
0.8072	Intermediate Similarity	NPC474686
0.8072	Intermediate Similarity	NPC470588
0.8072	Intermediate Similarity	NPC127689
0.8072	Intermediate Similarity	NPC290972
0.8072	Intermediate Similarity	NPC64872
0.8072	Intermediate Similarity	NPC270768
0.8072	Intermediate Similarity	NPC213832
0.8072	Intermediate Similarity	NPC263393
0.8072	Intermediate Similarity	NPC474700
0.8072	Intermediate Similarity	NPC274330
0.8072	Intermediate Similarity	NPC271974
0.8072	Intermediate Similarity	NPC474972
0.8072	Intermediate Similarity	NPC220498
0.8072	Intermediate Similarity	NPC121798
0.8072	Intermediate Similarity	NPC95246
0.8072	Intermediate Similarity	NPC281524
0.8072	Intermediate Similarity	NPC234346
0.8072	Intermediate Similarity	NPC130520
0.8072	Intermediate Similarity	NPC161751
0.8052	Intermediate Similarity	NPC239098
0.8052	Intermediate Similarity	NPC179028
0.8052	Intermediate Similarity	NPC321514
0.8049	Intermediate Similarity	NPC71507
0.8028	Intermediate Similarity	NPC42060
0.8	Intermediate Similarity	NPC472743
0.8	Intermediate Similarity	NPC475726
0.8	Intermediate Similarity	NPC162164
0.8	Intermediate Similarity	NPC166797
0.8	Intermediate Similarity	NPC175410
0.8	Intermediate Similarity	NPC301065
0.8	Intermediate Similarity	NPC215893
0.7976	Intermediate Similarity	NPC172361
0.7976	Intermediate Similarity	NPC18872
0.7976	Intermediate Similarity	NPC46441
0.7976	Intermediate Similarity	NPC290614
0.7976	Intermediate Similarity	NPC291028
0.7976	Intermediate Similarity	NPC113989
0.7976	Intermediate Similarity	NPC7260
0.7976	Intermediate Similarity	NPC227467
0.7976	Intermediate Similarity	NPC193750
0.7976	Intermediate Similarity	NPC126369
0.7976	Intermediate Similarity	NPC198818
0.7976	Intermediate Similarity	NPC130278
0.7976	Intermediate Similarity	NPC169933
0.7976	Intermediate Similarity	NPC474728
0.7976	Intermediate Similarity	NPC120968
0.7976	Intermediate Similarity	NPC474964
0.7976	Intermediate Similarity	NPC120840
0.7976	Intermediate Similarity	NPC477288
0.7976	Intermediate Similarity	NPC210037
0.7976	Intermediate Similarity	NPC477872
0.7976	Intermediate Similarity	NPC111110
0.7976	Intermediate Similarity	NPC86372

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 NPC36310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	2306
0.2-0.3	4164
0.3-0.4	1661
0.4-0.5	452
0.5-0.6	242
0.6-0.7	107
0.7-0.8	15
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8481	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD8035	Phase 2
0.7882	Intermediate Similarity	NPD8034	Phase 2
0.7882	Intermediate Similarity	NPD7515	Phase 2
0.7778	Intermediate Similarity	NPD4224	Phase 2
0.7701	Intermediate Similarity	NPD7748	Approved
0.7647	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4788	Approved
0.75	Intermediate Similarity	NPD6081	Approved
0.7444	Intermediate Similarity	NPD7902	Approved
0.7326	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4786	Approved
0.7229	Intermediate Similarity	NPD4221	Approved
0.7229	Intermediate Similarity	NPD4223	Phase 3
0.7229	Intermediate Similarity	NPD3667	Approved
0.7195	Intermediate Similarity	NPD4695	Discontinued
0.7191	Intermediate Similarity	NPD6399	Phase 3
0.7176	Intermediate Similarity	NPD5329	Approved
0.716	Intermediate Similarity	NPD3617	Approved
0.7143	Intermediate Similarity	NPD7614	Phase 1
0.7125	Intermediate Similarity	NPD6117	Approved
0.7111	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7900	Approved
0.7105	Intermediate Similarity	NPD5360	Phase 3
0.7105	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6098	Approved
0.7093	Intermediate Similarity	NPD7521	Approved
0.7093	Intermediate Similarity	NPD7334	Approved
0.7093	Intermediate Similarity	NPD7146	Approved
0.7093	Intermediate Similarity	NPD6409	Approved
0.7093	Intermediate Similarity	NPD6684	Approved
0.7093	Intermediate Similarity	NPD5330	Approved
0.7059	Intermediate Similarity	NPD4197	Approved
0.7059	Intermediate Similarity	NPD3665	Phase 1
0.7059	Intermediate Similarity	NPD3133	Approved
0.7059	Intermediate Similarity	NPD3666	Approved
0.7037	Intermediate Similarity	NPD6116	Phase 1
0.7011	Intermediate Similarity	NPD3573	Approved
0.6951	Remote Similarity	NPD6697	Approved
0.6951	Remote Similarity	NPD6118	Approved
0.6951	Remote Similarity	NPD6115	Approved
0.6951	Remote Similarity	NPD6114	Approved
0.6932	Remote Similarity	NPD5737	Approved
0.6932	Remote Similarity	NPD6672	Approved
0.6932	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD4244	Approved
0.6923	Remote Similarity	NPD4245	Approved
0.6923	Remote Similarity	NPD4789	Approved
0.6897	Remote Similarity	NPD4690	Approved
0.6897	Remote Similarity	NPD4688	Approved
0.6897	Remote Similarity	NPD4689	Approved
0.6897	Remote Similarity	NPD3618	Phase 1
0.6897	Remote Similarity	NPD4693	Phase 3
0.6897	Remote Similarity	NPD5205	Approved
0.6897	Remote Similarity	NPD4519	Discontinued
0.6897	Remote Similarity	NPD4138	Approved
0.6897	Remote Similarity	NPD4623	Approved
0.6889	Remote Similarity	NPD5281	Approved
0.6889	Remote Similarity	NPD5284	Approved
0.6882	Remote Similarity	NPD6083	Phase 2
0.6882	Remote Similarity	NPD6084	Phase 2
0.6867	Remote Similarity	NPD7645	Phase 2
0.6854	Remote Similarity	NPD6673	Approved
0.6854	Remote Similarity	NPD6904	Approved
0.6854	Remote Similarity	NPD6080	Approved
0.6854	Remote Similarity	NPD5328	Approved
0.6835	Remote Similarity	NPD5777	Approved
0.6835	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3698	Phase 2
0.6795	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3702	Approved
0.6742	Remote Similarity	NPD5208	Approved
0.6711	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4139	Approved
0.6706	Remote Similarity	NPD4692	Approved
0.6705	Remote Similarity	NPD5690	Phase 2
0.6705	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4694	Approved
0.6705	Remote Similarity	NPD5280	Approved
0.6703	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD3668	Phase 3
0.6632	Remote Similarity	NPD5696	Approved
0.6632	Remote Similarity	NPD7638	Approved
0.6625	Remote Similarity	NPD4758	Discontinued
0.6625	Remote Similarity	NPD4243	Approved
0.6596	Remote Similarity	NPD7732	Phase 3
0.6582	Remote Similarity	NPD4137	Phase 3
0.6562	Remote Similarity	NPD7639	Approved
0.6562	Remote Similarity	NPD6404	Discontinued
0.6562	Remote Similarity	NPD7640	Approved
0.6522	Remote Similarity	NPD6050	Approved
0.6522	Remote Similarity	NPD5693	Phase 1
0.6522	Remote Similarity	NPD6411	Approved
0.6517	Remote Similarity	NPD5279	Phase 3
0.65	Remote Similarity	NPD4747	Approved
0.65	Remote Similarity	NPD4691	Approved
0.6489	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4195	Approved
0.6463	Remote Similarity	NPD4785	Approved
0.6463	Remote Similarity	NPD4784	Approved
0.6456	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4202	Approved
0.6413	Remote Similarity	NPD5207	Approved
0.6413	Remote Similarity	NPD5692	Phase 3
0.64	Remote Similarity	NPD5739	Approved
0.64	Remote Similarity	NPD6402	Approved
0.64	Remote Similarity	NPD7128	Approved
0.64	Remote Similarity	NPD6675	Approved
0.6395	Remote Similarity	NPD7525	Registered
0.6386	Remote Similarity	NPD7339	Approved
0.6386	Remote Similarity	NPD3703	Phase 2
0.6386	Remote Similarity	NPD6942	Approved
0.6383	Remote Similarity	NPD6001	Approved
0.6353	Remote Similarity	NPD5364	Discontinued
0.6344	Remote Similarity	NPD5694	Approved
0.6316	Remote Similarity	NPD5210	Approved
0.6316	Remote Similarity	NPD4629	Approved
0.631	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6101	Approved
0.6304	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD8133	Approved
0.6282	Remote Similarity	NPD7341	Phase 2
0.6275	Remote Similarity	NPD7320	Approved
0.6275	Remote Similarity	NPD6899	Approved
0.6275	Remote Similarity	NPD6881	Approved
0.6269	Remote Similarity	NPD634	Phase 3
0.6265	Remote Similarity	NPD5733	Approved
0.6265	Remote Similarity	NPD4058	Approved
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD3196	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD3194	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3195	Phase 2
0.625	Remote Similarity	NPD4266	Approved
0.6237	Remote Similarity	NPD4096	Approved
0.6214	Remote Similarity	NPD6372	Approved
0.6214	Remote Similarity	NPD6373	Approved
0.6203	Remote Similarity	NPD7331	Phase 2
0.6197	Remote Similarity	NPD3186	Phase 1
0.619	Remote Similarity	NPD4190	Phase 3
0.619	Remote Similarity	NPD8039	Approved
0.619	Remote Similarity	NPD5275	Approved
0.6186	Remote Similarity	NPD5173	Approved
0.6186	Remote Similarity	NPD4755	Approved
0.6176	Remote Similarity	NPD5697	Approved
0.6176	Remote Similarity	NPD6412	Phase 2
0.6176	Remote Similarity	NPD5701	Approved
0.6163	Remote Similarity	NPD3671	Phase 1
0.6163	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD6883	Approved
0.6136	Remote Similarity	NPD8028	Phase 2
0.6136	Remote Similarity	NPD857	Phase 3
0.6117	Remote Similarity	NPD6011	Approved
0.6117	Remote Similarity	NPD6686	Approved
0.6111	Remote Similarity	NPD3172	Approved
0.6105	Remote Similarity	NPD5133	Approved
0.61	Remote Similarity	NPD7632	Discontinued
0.6095	Remote Similarity	NPD6650	Approved
0.6095	Remote Similarity	NPD6617	Approved
0.6095	Remote Similarity	NPD8130	Phase 1
0.6095	Remote Similarity	NPD6649	Approved
0.6095	Remote Similarity	NPD6847	Approved
0.6095	Remote Similarity	NPD6869	Approved
0.6095	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD622	Approved
0.6071	Remote Similarity	NPD4687	Approved
0.6071	Remote Similarity	NPD6924	Approved
0.6071	Remote Similarity	NPD6926	Approved
0.6061	Remote Similarity	NPD5286	Approved
0.6061	Remote Similarity	NPD4700	Approved
0.6061	Remote Similarity	NPD5285	Approved
0.6061	Remote Similarity	NPD4696	Approved
0.6058	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6013	Approved
0.6058	Remote Similarity	NPD6014	Approved
0.6058	Remote Similarity	NPD6012	Approved
0.604	Remote Similarity	NPD6052	Approved
0.6038	Remote Similarity	NPD6882	Approved
0.6038	Remote Similarity	NPD8297	Approved
0.6027	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD5276	Approved
0.6022	Remote Similarity	NPD4518	Approved
0.6	Remote Similarity	NPD5223	Approved
0.5979	Remote Similarity	NPD5654	Approved
0.5963	Remote Similarity	NPD7115	Discovery
0.5963	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6051	Approved
0.5941	Remote Similarity	NPD4633	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