NPASS Compound

Structure

NPC89294 OpenBabel07101719402D 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 4.6960 -0.3559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1821 0.4861 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 -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 -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 4.2098 1.4583 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 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 3.3679 0.0000 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 -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 0 0 0 0 0 0 0 0 0 0 2.5259 0.4861 0.0000 C 0 0 0 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 4.2098 0.4861 0.0000 C 0 0 0 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 20 2 0 0 0 0 2 20 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 24 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 25 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 27 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 23 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 21 28 1 6 0 0 0 22 23 2 0 0 0 0 22 29 1 0 0 0 0 23 27 1 0 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 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:	6.794
LogD:	4.813
LogS:	-6.256
# 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:	0.444
Synthetic Accessibility Score:	4.697
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.383
MDCK Permeability:	1.0831544386746828e-05
Pgp-inhibitor:	0.09
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.775
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	95.56947326660156%
Volume Distribution (VD):	0.868
Pgp-substrate:	2.5400702953338623%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.395
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.612
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.298

ADMET: Excretion

Clearance (CL):	4.47
Half-life (T1/2):	0.101

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.447
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.309
Skin Sensitization:	0.1
Carcinogencity:	0.099
Eye Corrosion:	0.025
Eye Irritation:	0.081
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC89294

Natural Product ID:	NPC89294
*Common Name:**	3,4-Seco-Olean-4(23),13(18)-Dien-3-Oic Acid
IUPAC Name:	3-[(1S,2S,4aR,4bS,6aR,12aR)-1,4a,4b,6a,9,9-hexamethyl-2-prop-1-en-2-yl-3,4,5,6,7,8,10,11,12,12a-decahydro-2H-chrysen-1-yl]propanoic acid
Synonyms:
Standard InCHIKey:	UPKROLOLJKAWPU-NFNMRRJISA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-20(2)21-11-14-30(8)24(28(21,6)13-12-25(31)32)10-9-22-23-19-26(3,4)15-16-27(23,5)17-18-29(22,30)7/h21,24H,1,9-19H2,2-8H3,(H,31,32)/t21-,24+,27+,28-,29+,30+/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)[C@H](CCC3=C4CC(C)(C)CC[C@]4(C)CC[C@@]23C)[C@@]1(C)CCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376338
PubChem CID:	16215417
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	=	27500.0	nM	PMID[529320]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	28000.0	nM	PMID[529320]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	37400.0	nM	PMID[529320]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	38100.0	nM	PMID[529320]
NPT27	Others	Unspecified		IC50	=	58000.0	nM	PMID[529320]
NPT27	Others	Unspecified		IC50	=	36300.0	nM	PMID[529320]
NPT27	Others	Unspecified		IC50	=	25900.0	nM	PMID[529320]
NPT27	Others	Unspecified		IC50	=	24800.0	nM	PMID[529320]

☑ 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 NPC89294 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	176
0.1-0.2	1398
0.2-0.3	7059
0.3-0.4	16045
0.4-0.5	7296
0.5-0.6	5489
0.6-0.7	3883
0.7-0.8	1046
0.8-0.85	243
0.85-0.9	27
0.9-0.95	26
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC471899
0.9859	High Similarity	NPC107039
0.9859	High Similarity	NPC471897
0.9722	High Similarity	NPC260385
0.9722	High Similarity	NPC280654
0.9722	High Similarity	NPC110094
0.9589	High Similarity	NPC199595
0.9589	High Similarity	NPC231431
0.9589	High Similarity	NPC16394
0.9459	High Similarity	NPC104545
0.9459	High Similarity	NPC37038
0.9333	High Similarity	NPC471898
0.9333	High Similarity	NPC267691
0.9333	High Similarity	NPC274050
0.9333	High Similarity	NPC162632
0.9333	High Similarity	NPC263272
0.9333	High Similarity	NPC221647
0.9333	High Similarity	NPC142244
0.9306	High Similarity	NPC192540
0.9306	High Similarity	NPC279666
0.9296	High Similarity	NPC36310
0.9211	High Similarity	NPC251779
0.9211	High Similarity	NPC69101
0.92	High Similarity	NPC477057
0.9178	High Similarity	NPC69143
0.9167	High Similarity	NPC161923
0.9167	High Similarity	NPC103958
0.9167	High Similarity	NPC183503
0.9167	High Similarity	NPC251970
0.9167	High Similarity	NPC476046
0.9167	High Similarity	NPC241854
0.9167	High Similarity	NPC283908
0.9155	High Similarity	NPC160817
0.9091	High Similarity	NPC200752
0.9091	High Similarity	NPC70834
0.8974	High Similarity	NPC96095
0.8974	High Similarity	NPC477289
0.8974	High Similarity	NPC156981
0.8919	High Similarity	NPC309399
0.8904	High Similarity	NPC255168
0.8861	High Similarity	NPC474537
0.8831	High Similarity	NPC278459
0.8831	High Similarity	NPC147066
0.88	High Similarity	NPC165711
0.88	High Similarity	NPC68828
0.8784	High Similarity	NPC476844
0.8784	High Similarity	NPC201027
0.8767	High Similarity	NPC244708
0.8767	High Similarity	NPC161187
0.8767	High Similarity	NPC330659
0.875	High Similarity	NPC324063
0.8732	High Similarity	NPC36616
0.8732	High Similarity	NPC290445
0.8701	High Similarity	NPC267517
0.8684	High Similarity	NPC321514
0.8684	High Similarity	NPC179028
0.8667	High Similarity	NPC246445
0.8649	High Similarity	NPC166797
0.8649	High Similarity	NPC301065
0.8649	High Similarity	NPC237591
0.8649	High Similarity	NPC3753
0.8642	High Similarity	NPC293564
0.8642	High Similarity	NPC68160
0.8642	High Similarity	NPC158141
0.8642	High Similarity	NPC173089
0.8642	High Similarity	NPC307426
0.8642	High Similarity	NPC242468
0.8642	High Similarity	NPC98442
0.8642	High Similarity	NPC130577
0.8642	High Similarity	NPC102683
0.8642	High Similarity	NPC18064
0.8642	High Similarity	NPC51700
0.8642	High Similarity	NPC88716
0.8642	High Similarity	NPC171203
0.8642	High Similarity	NPC142415
0.8642	High Similarity	NPC71507
0.8608	High Similarity	NPC167103
0.859	High Similarity	NPC38350
0.859	High Similarity	NPC201912
0.859	High Similarity	NPC3915
0.8571	High Similarity	NPC327674
0.8571	High Similarity	NPC192744
0.8571	High Similarity	NPC477371
0.8571	High Similarity	NPC158846
0.8553	High Similarity	NPC66105
0.8537	High Similarity	NPC474474
0.8537	High Similarity	NPC52169
0.8537	High Similarity	NPC40552
0.8537	High Similarity	NPC181225
0.8537	High Similarity	NPC470629
0.8537	High Similarity	NPC290690
0.8537	High Similarity	NPC182797
0.8537	High Similarity	NPC1753
0.8537	High Similarity	NPC474511
0.8537	High Similarity	NPC17733
0.8537	High Similarity	NPC246708
0.8537	High Similarity	NPC473242
0.8537	High Similarity	NPC474512
0.8533	High Similarity	NPC476795
0.8519	High Similarity	NPC72638
0.85	High Similarity	NPC171789
0.8493	Intermediate Similarity	NPC91369
0.8481	Intermediate Similarity	NPC310989
0.8481	Intermediate Similarity	NPC260956
0.8481	Intermediate Similarity	NPC320514
0.8442	Intermediate Similarity	NPC239098
0.8434	Intermediate Similarity	NPC474686
0.8434	Intermediate Similarity	NPC161751
0.8434	Intermediate Similarity	NPC130520
0.8434	Intermediate Similarity	NPC290972
0.8434	Intermediate Similarity	NPC274330
0.8434	Intermediate Similarity	NPC121798
0.8434	Intermediate Similarity	NPC263393
0.8434	Intermediate Similarity	NPC64872
0.8434	Intermediate Similarity	NPC95246
0.8434	Intermediate Similarity	NPC127689
0.8434	Intermediate Similarity	NPC470588
0.8434	Intermediate Similarity	NPC474972
0.8434	Intermediate Similarity	NPC474700
0.8434	Intermediate Similarity	NPC281524
0.8434	Intermediate Similarity	NPC61543
0.8434	Intermediate Similarity	NPC59263
0.8434	Intermediate Similarity	NPC293048
0.8434	Intermediate Similarity	NPC225585
0.8434	Intermediate Similarity	NPC234346
0.8434	Intermediate Similarity	NPC270768
0.8434	Intermediate Similarity	NPC25906
0.8434	Intermediate Similarity	NPC198664
0.8434	Intermediate Similarity	NPC143232
0.8434	Intermediate Similarity	NPC477973
0.8421	Intermediate Similarity	NPC180886
0.8421	Intermediate Similarity	NPC899
0.8395	Intermediate Similarity	NPC29447
0.8378	Intermediate Similarity	NPC72343
0.8375	Intermediate Similarity	NPC53733
0.8375	Intermediate Similarity	NPC215893
0.8375	Intermediate Similarity	NPC83569
0.8375	Intermediate Similarity	NPC307258
0.8375	Intermediate Similarity	NPC69279
0.8354	Intermediate Similarity	NPC327002
0.8354	Intermediate Similarity	NPC477372
0.8333	Intermediate Similarity	NPC46441
0.8333	Intermediate Similarity	NPC470589
0.8333	Intermediate Similarity	NPC126369
0.8333	Intermediate Similarity	NPC210037
0.8333	Intermediate Similarity	NPC111110
0.8333	Intermediate Similarity	NPC477872
0.8333	Intermediate Similarity	NPC273621
0.8333	Intermediate Similarity	NPC7260
0.8333	Intermediate Similarity	NPC86372
0.8333	Intermediate Similarity	NPC474728
0.8333	Intermediate Similarity	NPC198818
0.8333	Intermediate Similarity	NPC215843
0.8333	Intermediate Similarity	NPC172361
0.8333	Intermediate Similarity	NPC474964
0.8333	Intermediate Similarity	NPC193750
0.8333	Intermediate Similarity	NPC192329
0.8333	Intermediate Similarity	NPC18872
0.8333	Intermediate Similarity	NPC120968
0.8333	Intermediate Similarity	NPC113989
0.8333	Intermediate Similarity	NPC130278
0.8333	Intermediate Similarity	NPC120840
0.8333	Intermediate Similarity	NPC290614
0.8333	Intermediate Similarity	NPC291028
0.8333	Intermediate Similarity	NPC477288
0.8333	Intermediate Similarity	NPC227467
0.8312	Intermediate Similarity	NPC212661
0.8312	Intermediate Similarity	NPC471035
0.8312	Intermediate Similarity	NPC61952
0.8312	Intermediate Similarity	NPC472300
0.8293	Intermediate Similarity	NPC322159
0.8293	Intermediate Similarity	NPC155011
0.8293	Intermediate Similarity	NPC73038
0.8293	Intermediate Similarity	NPC325594
0.8293	Intermediate Similarity	NPC56588
0.8272	Intermediate Similarity	NPC180834
0.8272	Intermediate Similarity	NPC248758
0.8272	Intermediate Similarity	NPC312660
0.8267	Intermediate Similarity	NPC35656
0.8267	Intermediate Similarity	NPC279241
0.825	Intermediate Similarity	NPC133391
0.825	Intermediate Similarity	NPC238991
0.825	Intermediate Similarity	NPC302661
0.8243	Intermediate Similarity	NPC235586
0.8235	Intermediate Similarity	NPC306541
0.8235	Intermediate Similarity	NPC285184
0.8235	Intermediate Similarity	NPC6255
0.8235	Intermediate Similarity	NPC25299
0.8235	Intermediate Similarity	NPC228784
0.8235	Intermediate Similarity	NPC233455
0.8235	Intermediate Similarity	NPC60755
0.8235	Intermediate Similarity	NPC71074
0.8235	Intermediate Similarity	NPC966
0.8235	Intermediate Similarity	NPC230064
0.8235	Intermediate Similarity	NPC84319
0.8235	Intermediate Similarity	NPC38754
0.8235	Intermediate Similarity	NPC145067
0.8235	Intermediate Similarity	NPC288833
0.8235	Intermediate Similarity	NPC472149
0.8235	Intermediate Similarity	NPC324341

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 NPC89294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1814
0.2-0.3	4051
0.3-0.4	2086
0.4-0.5	568
0.5-0.6	246
0.6-0.7	152
0.7-0.8	54
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD7515	Phase 2
0.8214	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7748	Approved
0.7952	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD4786	Approved
0.7805	Intermediate Similarity	NPD3667	Approved
0.7805	Intermediate Similarity	NPD4223	Phase 3
0.7805	Intermediate Similarity	NPD4221	Approved
0.7778	Intermediate Similarity	NPD7902	Approved
0.7778	Intermediate Similarity	NPD4695	Discontinued
0.775	Intermediate Similarity	NPD3617	Approved
0.7738	Intermediate Similarity	NPD5329	Approved
0.7727	Intermediate Similarity	NPD6399	Phase 3
0.7667	Intermediate Similarity	NPD7614	Phase 1
0.7647	Intermediate Similarity	NPD6684	Approved
0.7647	Intermediate Similarity	NPD5330	Approved
0.7647	Intermediate Similarity	NPD6098	Approved
0.7647	Intermediate Similarity	NPD7521	Approved
0.7647	Intermediate Similarity	NPD7334	Approved
0.7647	Intermediate Similarity	NPD7146	Approved
0.7647	Intermediate Similarity	NPD6409	Approved
0.7619	Intermediate Similarity	NPD3133	Approved
0.7619	Intermediate Similarity	NPD3666	Approved
0.7619	Intermediate Similarity	NPD4197	Approved
0.7619	Intermediate Similarity	NPD3665	Phase 1
0.7558	Intermediate Similarity	NPD3573	Approved
0.7471	Intermediate Similarity	NPD5737	Approved
0.7471	Intermediate Similarity	NPD6672	Approved
0.7471	Intermediate Similarity	NPD6903	Approved
0.7467	Intermediate Similarity	NPD4224	Phase 2
0.7444	Intermediate Similarity	NPD7900	Approved
0.7444	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3618	Phase 1
0.7442	Intermediate Similarity	NPD4689	Approved
0.7442	Intermediate Similarity	NPD4623	Approved
0.7442	Intermediate Similarity	NPD4690	Approved
0.7442	Intermediate Similarity	NPD5205	Approved
0.7442	Intermediate Similarity	NPD4519	Discontinued
0.7442	Intermediate Similarity	NPD4688	Approved
0.7442	Intermediate Similarity	NPD4138	Approved
0.7442	Intermediate Similarity	NPD4693	Phase 3
0.7416	Intermediate Similarity	NPD8035	Phase 2
0.7416	Intermediate Similarity	NPD8034	Phase 2
0.7416	Intermediate Similarity	NPD5281	Approved
0.7416	Intermediate Similarity	NPD5284	Approved
0.7391	Intermediate Similarity	NPD6084	Phase 2
0.7391	Intermediate Similarity	NPD6083	Phase 2
0.7386	Intermediate Similarity	NPD5328	Approved
0.7386	Intermediate Similarity	NPD6904	Approved
0.7386	Intermediate Similarity	NPD6080	Approved
0.7386	Intermediate Similarity	NPD6673	Approved
0.7294	Intermediate Similarity	NPD4788	Approved
0.7273	Intermediate Similarity	NPD5208	Approved
0.7262	Intermediate Similarity	NPD4692	Approved
0.7262	Intermediate Similarity	NPD4139	Approved
0.7241	Intermediate Similarity	NPD5280	Approved
0.7241	Intermediate Similarity	NPD4694	Approved
0.7241	Intermediate Similarity	NPD5690	Phase 2
0.7241	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7645	Phase 2
0.7222	Intermediate Similarity	NPD6079	Approved
0.7215	Intermediate Similarity	NPD4243	Approved
0.7215	Intermediate Similarity	NPD6081	Approved
0.7209	Intermediate Similarity	NPD3668	Phase 3
0.7191	Intermediate Similarity	NPD4753	Phase 2
0.7179	Intermediate Similarity	NPD4137	Phase 3
0.7176	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5695	Phase 3
0.7128	Intermediate Similarity	NPD5696	Approved
0.7097	Intermediate Similarity	NPD7732	Phase 3
0.7089	Intermediate Similarity	NPD4691	Approved
0.7089	Intermediate Similarity	NPD4747	Approved
0.7053	Intermediate Similarity	NPD6404	Discontinued
0.7051	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5279	Phase 3
0.7037	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4784	Approved
0.7037	Intermediate Similarity	NPD4785	Approved
0.7033	Intermediate Similarity	NPD6050	Approved
0.7033	Intermediate Similarity	NPD6411	Approved
0.7033	Intermediate Similarity	NPD5693	Phase 1
0.7024	Intermediate Similarity	NPD4195	Approved
0.6989	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4202	Approved
0.6951	Remote Similarity	NPD6942	Approved
0.6951	Remote Similarity	NPD7339	Approved
0.6947	Remote Similarity	NPD7638	Approved
0.6923	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD5692	Phase 3
0.6883	Remote Similarity	NPD7341	Phase 2
0.6882	Remote Similarity	NPD6001	Approved
0.6875	Remote Similarity	NPD7640	Approved
0.6875	Remote Similarity	NPD7639	Approved
0.6869	Remote Similarity	NPD6402	Approved
0.6869	Remote Similarity	NPD7128	Approved
0.6869	Remote Similarity	NPD5739	Approved
0.6869	Remote Similarity	NPD6675	Approved
0.6867	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6117	Approved
0.6848	Remote Similarity	NPD5694	Approved
0.6835	Remote Similarity	NPD5360	Phase 3
0.6835	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4058	Approved
0.6829	Remote Similarity	NPD5733	Approved
0.6813	Remote Similarity	NPD6101	Approved
0.6813	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4629	Approved
0.6809	Remote Similarity	NPD5210	Approved
0.6795	Remote Similarity	NPD7331	Phase 2
0.6786	Remote Similarity	NPD6116	Phase 1
0.6747	Remote Similarity	NPD8039	Approved
0.6747	Remote Similarity	NPD5275	Approved
0.6747	Remote Similarity	NPD4190	Phase 3
0.6744	Remote Similarity	NPD7525	Registered
0.6739	Remote Similarity	NPD4096	Approved
0.6737	Remote Similarity	NPD4697	Phase 3
0.6737	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5222	Approved
0.6737	Remote Similarity	NPD5221	Approved
0.6733	Remote Similarity	NPD7320	Approved
0.6733	Remote Similarity	NPD6881	Approved
0.6733	Remote Similarity	NPD6899	Approved
0.6706	Remote Similarity	NPD6118	Approved
0.6706	Remote Similarity	NPD6114	Approved
0.6706	Remote Similarity	NPD6115	Approved
0.6706	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD3196	Approved
0.6667	Remote Similarity	NPD3195	Phase 2
0.6667	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD3194	Approved
0.6667	Remote Similarity	NPD8028	Phase 2
0.6667	Remote Similarity	NPD4266	Approved
0.6634	Remote Similarity	NPD5701	Approved
0.6634	Remote Similarity	NPD6412	Phase 2
0.6634	Remote Similarity	NPD5697	Approved
0.6627	Remote Similarity	NPD4687	Approved
0.6602	Remote Similarity	NPD7102	Approved
0.6602	Remote Similarity	NPD6883	Approved
0.6602	Remote Similarity	NPD7290	Approved
0.6596	Remote Similarity	NPD5133	Approved
0.6585	Remote Similarity	NPD5276	Approved
0.6585	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5777	Approved
0.6585	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6011	Approved
0.6548	Remote Similarity	NPD3702	Approved
0.6543	Remote Similarity	NPD3698	Phase 2
0.6543	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6869	Approved
0.6538	Remote Similarity	NPD6847	Approved
0.6538	Remote Similarity	NPD6649	Approved
0.6538	Remote Similarity	NPD8130	Phase 1
0.6538	Remote Similarity	NPD6650	Approved
0.6538	Remote Similarity	NPD6617	Approved
0.6538	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4696	Approved
0.6531	Remote Similarity	NPD5286	Approved
0.6531	Remote Similarity	NPD4700	Approved
0.6531	Remote Similarity	NPD5285	Approved
0.6528	Remote Similarity	NPD3172	Approved
0.6522	Remote Similarity	NPD4518	Approved
0.6512	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6014	Approved
0.6505	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6012	Approved
0.6505	Remote Similarity	NPD6013	Approved
0.65	Remote Similarity	NPD6052	Approved
0.6477	Remote Similarity	NPD857	Phase 3
0.6476	Remote Similarity	NPD8297	Approved
0.6476	Remote Similarity	NPD6882	Approved
0.6465	Remote Similarity	NPD5223	Approved
0.6458	Remote Similarity	NPD5654	Approved
0.6456	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6051	Approved
0.6429	Remote Similarity	NPD6926	Approved
0.6429	Remote Similarity	NPD6924	Approved
0.6421	Remote Similarity	NPD5778	Approved
0.6421	Remote Similarity	NPD5779	Approved
0.6408	Remote Similarity	NPD6686	Approved
0.64	Remote Similarity	NPD5091	Approved
0.64	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD7632	Discontinued
0.64	Remote Similarity	NPD5224	Approved
0.64	Remote Similarity	NPD4633	Approved
0.64	Remote Similarity	NPD5225	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.6389	Remote Similarity	NPD7115	Discovery
0.6386	Remote Similarity	NPD4758	Discontinued
0.6374	Remote Similarity	NPD1694	Approved
0.6337	Remote Similarity	NPD5175	Approved
0.6337	Remote Similarity	NPD5174	Approved
0.6337	Remote Similarity	NPD4754	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