NPASS Compound

Structure

NPC3464 OpenBabel07101719512D 30 31 0 0 1 0 0 0 0 0999 V2000 4.1220 1.7005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7461 -1.6601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7787 2.3081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2081 -1.2760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0793 -1.4950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9668 1.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7778 -1.0443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4471 0.7238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3910 1.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3153 -0.8333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 -0.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7922 0.7129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1471 1.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3094 -0.8339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4669 1.1900 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2019 -1.0011 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4606 0.8876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8783 0.1418 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8523 2.8786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8534 1.3109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7081 -0.4100 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7018 -0.7124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3066 -0.9086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9071 -1.9567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5325 3.6117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8774 3.1011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 1.7448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7081 -0.4100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8755 0.0671 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 23 2 0 0 0 0 14 29 1 0 0 0 0 15 13 1 1 0 0 0 16 22 1 6 0 0 0 16 24 1 0 0 0 0 17 20 1 6 0 0 0 17 30 1 0 0 0 0 18 21 1 1 0 0 0 18 29 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 20 3 1 1 0 0 0 20 27 1 0 0 0 0 21 4 1 6 0 0 0 21 28 1 0 0 0 0 22 5 1 1 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.24
Volume:	434.368
LogP:	1.008
LogD:	0.403
LogS:	-2.299
# Rotatable Bonds:	4
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	5.883
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.295
MDCK Permeability:	4.1611747292336076e-05
Pgp-inhibitor:	0.595
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.578
20% Bioavailability (F20%):	0.344
30% Bioavailability (F30%):	0.139

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177
Plasma Protein Binding (PPB):	56.4039306640625%
Volume Distribution (VD):	0.36
Pgp-substrate:	34.92527770996094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	2.462
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.349
Drug-inuced Liver Injury (DILI):	0.642
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.702
Maximum Recommended Daily Dose:	0.536
Skin Sensitization:	0.62
Carcinogencity:	0.79
Eye Corrosion:	0.066
Eye Irritation:	0.349
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC3464

Natural Product ID:	NPC3464
*Common Name:**	Dendronpholide J
IUPAC Name:	2-[(1S,2R,5R,7R,8S,11S,12R)-7-acetyloxy-2,8,11-trihydroxy-2,8,12-trimethyl-15-oxabicyclo[10.2.1]pentadecan-5-yl]prop-2-enoic acid
Synonyms:	Dendronpholide J
Standard InCHIKey:	DTBIJVSZQRYFFB-XHMTVPDMSA-N
Standard InCHI:	InChI=1S/C22H36O8/c1-13(19(25)26)15-6-9-20(3,27)17-8-11-22(5,30-17)16(24)7-10-21(4,28)18(12-15)29-14(2)23/h15-18,24,27-28H,1,6-12H2,2-5H3,(H,25,26)/t15-,16+,17+,18-,20-,21+,22-/m1/s1
SMILES:	C=C([C@@H]1CC[C@](C)([C@@H]2CC[C@](C)([C@H](CC[C@@](C)([C@@H](C1)OC(=O)C)O)O)O2)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521100
PubChem CID:	44568406
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33216	dendronephthya sp.	Species	Nephtheidae	Eukaryota	n.a.	chinese soft coral	n.a.	PMID[18563933]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.2	ug.mL-1	PMID[493125]

☑ 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 NPC3464 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	203
0.1-0.2	1581
0.2-0.3	5616
0.3-0.4	13040
0.4-0.5	10185
0.5-0.6	7692
0.6-0.7	3549
0.7-0.8	749
0.8-0.85	54
0.85-0.9	20
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475963
1.0	High Similarity	NPC151176
0.95	High Similarity	NPC474780
0.9268	High Similarity	NPC476015
0.9268	High Similarity	NPC475019
0.9268	High Similarity	NPC474762
0.9268	High Similarity	NPC474949
0.9167	High Similarity	NPC92974
0.9146	High Similarity	NPC47958
0.9146	High Similarity	NPC304509
0.9146	High Similarity	NPC149725
0.9146	High Similarity	NPC329749
0.9048	High Similarity	NPC177629
0.9048	High Similarity	NPC58219
0.8929	High Similarity	NPC186148
0.8864	High Similarity	NPC36954
0.8837	High Similarity	NPC476004
0.8837	High Similarity	NPC474761
0.8736	High Similarity	NPC30515
0.8736	High Similarity	NPC184463
0.8721	High Similarity	NPC307411
0.8636	High Similarity	NPC475912
0.8636	High Similarity	NPC476300
0.8621	High Similarity	NPC51004
0.8605	High Similarity	NPC202672
0.8556	High Similarity	NPC470883
0.8556	High Similarity	NPC158416
0.8556	High Similarity	NPC476315
0.8556	High Similarity	NPC39859
0.8556	High Similarity	NPC76862
0.8539	High Similarity	NPC474035
0.8539	High Similarity	NPC190294
0.8539	High Similarity	NPC81386
0.8537	High Similarity	NPC474981
0.8523	High Similarity	NPC208886
0.8523	High Similarity	NPC12172
0.8506	High Similarity	NPC474951
0.8506	High Similarity	NPC173926
0.8488	Intermediate Similarity	NPC248602
0.8471	Intermediate Similarity	NPC137033
0.8462	Intermediate Similarity	NPC328562
0.8462	Intermediate Similarity	NPC323421
0.8452	Intermediate Similarity	NPC257358
0.8452	Intermediate Similarity	NPC474472
0.8452	Intermediate Similarity	NPC11620
0.8444	Intermediate Similarity	NPC14961
0.8444	Intermediate Similarity	NPC270013
0.8427	Intermediate Similarity	NPC81419
0.8427	Intermediate Similarity	NPC212486
0.8427	Intermediate Similarity	NPC179746
0.8391	Intermediate Similarity	NPC227379
0.8391	Intermediate Similarity	NPC474471
0.8391	Intermediate Similarity	NPC153805
0.8352	Intermediate Similarity	NPC476009
0.8352	Intermediate Similarity	NPC31645
0.8315	Intermediate Similarity	NPC329952
0.8315	Intermediate Similarity	NPC475881
0.8315	Intermediate Similarity	NPC70251
0.8242	Intermediate Similarity	NPC475900
0.8202	Intermediate Similarity	NPC65359
0.8202	Intermediate Similarity	NPC206614
0.8202	Intermediate Similarity	NPC474323
0.8182	Intermediate Similarity	NPC281516
0.8172	Intermediate Similarity	NPC474213
0.8161	Intermediate Similarity	NPC470242
0.8148	Intermediate Similarity	NPC217725
0.814	Intermediate Similarity	NPC9868
0.8105	Intermediate Similarity	NPC320019
0.8105	Intermediate Similarity	NPC324017
0.809	Intermediate Similarity	NPC474032
0.8068	Intermediate Similarity	NPC190753
0.8068	Intermediate Similarity	NPC179659
0.8068	Intermediate Similarity	NPC5130
0.8065	Intermediate Similarity	NPC40812
0.8065	Intermediate Similarity	NPC471150
0.8046	Intermediate Similarity	NPC21469
0.8021	Intermediate Similarity	NPC472755
0.8	Intermediate Similarity	NPC473448
0.8	Intermediate Similarity	NPC15993
0.8	Intermediate Similarity	NPC475748
0.7978	Intermediate Similarity	NPC476704
0.7957	Intermediate Similarity	NPC279621
0.7955	Intermediate Similarity	NPC164393
0.7935	Intermediate Similarity	NPC57405
0.7935	Intermediate Similarity	NPC303942
0.7931	Intermediate Similarity	NPC243618
0.7931	Intermediate Similarity	NPC70424
0.7912	Intermediate Similarity	NPC469627
0.7912	Intermediate Similarity	NPC473321
0.7895	Intermediate Similarity	NPC288876
0.7889	Intermediate Similarity	NPC295312
0.7882	Intermediate Similarity	NPC103634
0.7872	Intermediate Similarity	NPC111348
0.7872	Intermediate Similarity	NPC474313
0.7865	Intermediate Similarity	NPC118601
0.7865	Intermediate Similarity	NPC231889
0.7849	Intermediate Similarity	NPC471142
0.7826	Intermediate Similarity	NPC162205
0.7826	Intermediate Similarity	NPC475788
0.7826	Intermediate Similarity	NPC295204
0.7826	Intermediate Similarity	NPC273579
0.7826	Intermediate Similarity	NPC288240
0.7816	Intermediate Similarity	NPC239308
0.7812	Intermediate Similarity	NPC47880
0.7812	Intermediate Similarity	NPC287539
0.7812	Intermediate Similarity	NPC3488
0.7812	Intermediate Similarity	NPC476270
0.7802	Intermediate Similarity	NPC473619
0.7802	Intermediate Similarity	NPC478004
0.7802	Intermediate Similarity	NPC471378
0.7802	Intermediate Similarity	NPC158388
0.7802	Intermediate Similarity	NPC312471
0.7802	Intermediate Similarity	NPC313670
0.7802	Intermediate Similarity	NPC478003
0.7791	Intermediate Similarity	NPC77003
0.7789	Intermediate Similarity	NPC83895
0.7789	Intermediate Similarity	NPC261377
0.7789	Intermediate Similarity	NPC187761
0.7789	Intermediate Similarity	NPC471144
0.7789	Intermediate Similarity	NPC308567
0.7789	Intermediate Similarity	NPC473326
0.7789	Intermediate Similarity	NPC187268
0.7789	Intermediate Similarity	NPC255592
0.7778	Intermediate Similarity	NPC89001
0.7778	Intermediate Similarity	NPC178875
0.7778	Intermediate Similarity	NPC207114
0.7778	Intermediate Similarity	NPC473715
0.7778	Intermediate Similarity	NPC217983
0.7766	Intermediate Similarity	NPC473859
0.7755	Intermediate Similarity	NPC100487
0.7753	Intermediate Similarity	NPC322922
0.7753	Intermediate Similarity	NPC321812
0.7753	Intermediate Similarity	NPC162071
0.7742	Intermediate Similarity	NPC474247
0.7742	Intermediate Similarity	NPC71589
0.7732	Intermediate Similarity	NPC474747
0.7732	Intermediate Similarity	NPC472754
0.7732	Intermediate Similarity	NPC80144
0.7732	Intermediate Similarity	NPC149371
0.7727	Intermediate Similarity	NPC472957
0.7727	Intermediate Similarity	NPC72464
0.7727	Intermediate Similarity	NPC472958
0.7722	Intermediate Similarity	NPC286842
0.7717	Intermediate Similarity	NPC476705
0.7717	Intermediate Similarity	NPC184063
0.7717	Intermediate Similarity	NPC471747
0.7708	Intermediate Similarity	NPC471381
0.7708	Intermediate Similarity	NPC186861
0.7692	Intermediate Similarity	NPC477017
0.7692	Intermediate Similarity	NPC477011
0.7692	Intermediate Similarity	NPC477016
0.7692	Intermediate Similarity	NPC151770
0.7677	Intermediate Similarity	NPC472749
0.7677	Intermediate Similarity	NPC243998
0.7677	Intermediate Similarity	NPC127235
0.7677	Intermediate Similarity	NPC472751
0.7677	Intermediate Similarity	NPC223450
0.7674	Intermediate Similarity	NPC233377
0.7674	Intermediate Similarity	NPC472948
0.766	Intermediate Similarity	NPC322188
0.766	Intermediate Similarity	NPC476053
0.766	Intermediate Similarity	NPC475659
0.766	Intermediate Similarity	NPC472873
0.7653	Intermediate Similarity	NPC37240
0.7653	Intermediate Similarity	NPC475945
0.7653	Intermediate Similarity	NPC475871
0.7647	Intermediate Similarity	NPC3852
0.764	Intermediate Similarity	NPC475206
0.764	Intermediate Similarity	NPC477018
0.764	Intermediate Similarity	NPC329838
0.764	Intermediate Similarity	NPC329615
0.764	Intermediate Similarity	NPC196911
0.764	Intermediate Similarity	NPC100921
0.764	Intermediate Similarity	NPC471379
0.7634	Intermediate Similarity	NPC228451
0.7634	Intermediate Similarity	NPC125674
0.7634	Intermediate Similarity	NPC475838
0.7629	Intermediate Similarity	NPC201718
0.7629	Intermediate Similarity	NPC472753
0.7629	Intermediate Similarity	NPC67296
0.7614	Intermediate Similarity	NPC272814
0.7614	Intermediate Similarity	NPC128246
0.7614	Intermediate Similarity	NPC250315
0.7614	Intermediate Similarity	NPC5958
0.7609	Intermediate Similarity	NPC475855
0.7609	Intermediate Similarity	NPC19087
0.7604	Intermediate Similarity	NPC300584
0.76	Intermediate Similarity	NPC477513
0.7586	Intermediate Similarity	NPC118116
0.7586	Intermediate Similarity	NPC126248
0.7582	Intermediate Similarity	NPC476708
0.7582	Intermediate Similarity	NPC92370
0.7582	Intermediate Similarity	NPC476706
0.7582	Intermediate Similarity	NPC476707
0.7579	Intermediate Similarity	NPC477921
0.7579	Intermediate Similarity	NPC474297
0.7579	Intermediate Similarity	NPC230800
0.7579	Intermediate Similarity	NPC161293
0.7576	Intermediate Similarity	NPC472748
0.7558	Intermediate Similarity	NPC19841

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 NPC3464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	2438
0.2-0.3	3669
0.3-0.4	1865
0.4-0.5	544
0.5-0.6	327
0.6-0.7	69
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7912	Intermediate Similarity	NPD7983	Approved
0.7609	Intermediate Similarity	NPD6698	Approved
0.7609	Intermediate Similarity	NPD46	Approved
0.7255	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7838	Discovery
0.7048	Intermediate Similarity	NPD6371	Approved
0.7019	Intermediate Similarity	NPD6686	Approved
0.6981	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6435	Approved
0.6914	Remote Similarity	NPD7909	Approved
0.6907	Remote Similarity	NPD5779	Approved
0.6907	Remote Similarity	NPD5778	Approved
0.69	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7154	Phase 3
0.6768	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4250	Approved
0.6737	Remote Similarity	NPD4251	Approved
0.6703	Remote Similarity	NPD5368	Approved
0.67	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD5362	Discontinued
0.6632	Remote Similarity	NPD4249	Approved
0.6632	Remote Similarity	NPD5786	Approved
0.6602	Remote Similarity	NPD5344	Discontinued
0.6598	Remote Similarity	NPD1695	Approved
0.6579	Remote Similarity	NPD8513	Phase 3
0.6579	Remote Similarity	NPD8516	Approved
0.6579	Remote Similarity	NPD8515	Approved
0.6579	Remote Similarity	NPD8517	Approved
0.6545	Remote Similarity	NPD8133	Approved
0.6545	Remote Similarity	NPD4632	Approved
0.6542	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5363	Approved
0.6522	Remote Similarity	NPD4819	Approved
0.6522	Remote Similarity	NPD4821	Approved
0.6522	Remote Similarity	NPD4822	Approved
0.6522	Remote Similarity	NPD4820	Approved
0.6522	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6319	Approved
0.6484	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6053	Discontinued
0.6455	Remote Similarity	NPD8297	Approved
0.6452	Remote Similarity	NPD5369	Approved
0.6429	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6101	Approved
0.6408	Remote Similarity	NPD4225	Approved
0.6383	Remote Similarity	NPD4269	Approved
0.6383	Remote Similarity	NPD4270	Approved
0.6364	Remote Similarity	NPD5785	Approved
0.6356	Remote Similarity	NPD7507	Approved
0.6346	Remote Similarity	NPD7639	Approved
0.6346	Remote Similarity	NPD7640	Approved
0.6337	Remote Similarity	NPD5282	Discontinued
0.633	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6110	Phase 1
0.6316	Remote Similarity	NPD7641	Discontinued
0.6304	Remote Similarity	NPD4268	Approved
0.6304	Remote Similarity	NPD4271	Approved
0.6303	Remote Similarity	NPD8074	Phase 3
0.63	Remote Similarity	NPD6411	Approved
0.6296	Remote Similarity	NPD6412	Phase 2
0.6271	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD7638	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6235	Remote Similarity	NPD7341	Phase 2
0.6228	Remote Similarity	NPD6009	Approved
0.6228	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6616	Approved
0.6216	Remote Similarity	NPD6649	Approved
0.6216	Remote Similarity	NPD6650	Approved
0.6207	Remote Similarity	NPD6054	Approved
0.6204	Remote Similarity	NPD6675	Approved
0.6204	Remote Similarity	NPD7128	Approved
0.6204	Remote Similarity	NPD5739	Approved
0.6204	Remote Similarity	NPD6402	Approved
0.6203	Remote Similarity	NPD3730	Approved
0.6203	Remote Similarity	NPD3728	Approved
0.6198	Remote Similarity	NPD7319	Approved
0.619	Remote Similarity	NPD6648	Approved
0.6186	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7604	Phase 2
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.617	Remote Similarity	NPD4252	Approved
0.6167	Remote Similarity	NPD7078	Approved
0.6163	Remote Similarity	NPD7331	Phase 2
0.6161	Remote Similarity	NPD6882	Approved
0.6154	Remote Similarity	NPD5983	Phase 2
0.6147	Remote Similarity	NPD5697	Approved
0.6146	Remote Similarity	NPD5332	Approved
0.6146	Remote Similarity	NPD5331	Approved
0.6139	Remote Similarity	NPD8035	Phase 2
0.6139	Remote Similarity	NPD8034	Phase 2
0.6134	Remote Similarity	NPD8299	Approved
0.6134	Remote Similarity	NPD8342	Approved
0.6134	Remote Similarity	NPD8340	Approved
0.6134	Remote Similarity	NPD8341	Approved
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6118	Remote Similarity	NPD3197	Phase 1
0.6116	Remote Similarity	NPD7736	Approved
0.6111	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4790	Discontinued
0.6102	Remote Similarity	NPD6370	Approved
0.6102	Remote Similarity	NPD8080	Discontinued
0.6092	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6011	Approved
0.6091	Remote Similarity	NPD7320	Approved
0.6087	Remote Similarity	NPD7115	Discovery
0.6083	Remote Similarity	NPD6336	Discontinued
0.6078	Remote Similarity	NPD6399	Phase 3
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6068	Remote Similarity	NPD6059	Approved
0.6061	Remote Similarity	NPD7524	Approved
0.6055	Remote Similarity	NPD6008	Approved
0.605	Remote Similarity	NPD7829	Approved
0.605	Remote Similarity	NPD8328	Phase 3
0.605	Remote Similarity	NPD7830	Approved
0.605	Remote Similarity	NPD7642	Approved
0.6042	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6012	Approved
0.6036	Remote Similarity	NPD6014	Approved
0.6036	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6013	Approved
0.6033	Remote Similarity	NPD8293	Discontinued
0.6024	Remote Similarity	NPD3198	Approved
0.602	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD8266	Approved
0.6017	Remote Similarity	NPD8267	Approved
0.6017	Remote Similarity	NPD6921	Approved
0.6017	Remote Similarity	NPD6016	Approved
0.6017	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6015	Approved
0.6017	Remote Similarity	NPD8268	Approved
0.6017	Remote Similarity	NPD8269	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6421	Discontinued
0.598	Remote Similarity	NPD7637	Suspended
0.5979	Remote Similarity	NPD4788	Approved
0.5966	Remote Similarity	NPD5988	Approved
0.5963	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6422	Discontinued
0.595	Remote Similarity	NPD8451	Approved
0.595	Remote Similarity	NPD8273	Phase 1
0.5948	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5211	Phase 2
0.5926	Remote Similarity	NPD8082	Approved
0.5926	Remote Similarity	NPD7632	Discontinued
0.5926	Remote Similarity	NPD8085	Approved
0.5926	Remote Similarity	NPD8138	Approved
0.5926	Remote Similarity	NPD8084	Approved
0.5926	Remote Similarity	NPD8139	Approved
0.5926	Remote Similarity	NPD8086	Approved
0.5926	Remote Similarity	NPD8083	Approved
0.5918	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD8448	Approved
0.5889	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8444	Approved
0.5872	Remote Similarity	NPD8275	Approved
0.5872	Remote Similarity	NPD8276	Approved
0.5865	Remote Similarity	NPD7748	Approved
0.5859	Remote Similarity	NPD1694	Approved
0.5856	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7902	Approved
0.5841	Remote Similarity	NPD4634	Approved
0.584	Remote Similarity	NPD7260	Phase 2
0.5825	Remote Similarity	NPD7515	Phase 2
0.5825	Remote Similarity	NPD6079	Approved
0.5818	Remote Similarity	NPD5141	Approved
0.5818	Remote Similarity	NPD8081	Approved
0.5816	Remote Similarity	NPD6695	Phase 3
0.581	Remote Similarity	NPD5695	Phase 3
0.58	Remote Similarity	NPD6409	Approved
0.58	Remote Similarity	NPD7334	Approved
0.58	Remote Similarity	NPD5330	Approved
0.58	Remote Similarity	NPD7521	Approved
0.58	Remote Similarity	NPD6684	Approved
0.58	Remote Similarity	NPD7146	Approved
0.5794	Remote Similarity	NPD6845	Suspended
0.5789	Remote Similarity	NPD4802	Phase 2
0.5789	Remote Similarity	NPD4238	Approved
0.5784	Remote Similarity	NPD5328	Approved
0.5784	Remote Similarity	NPD5370	Suspended
0.5766	Remote Similarity	NPD8393	Approved
0.5765	Remote Similarity	NPD1145	Discontinued
0.5763	Remote Similarity	NPD6335	Approved
0.5763	Remote Similarity	NPD7328	Approved
0.5763	Remote Similarity	NPD7327	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