NPASS Compound

Structure

NPC67653 OpenBabel07101718192D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.8344 2.2920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3605 -2.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0009 1.0659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5009 0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8250 0.5934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9870 1.3547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7967 -1.0198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7967 1.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5009 -0.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0925 -0.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0925 1.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5741 2.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7526 0.0995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2265 -0.3001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0715 2.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3605 -1.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6327 3.2478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7967 0.6065 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7526 1.9266 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3884 0.6065 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9599 0.2804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1302 2.6012 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0484 1.6173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5633 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5009 0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3884 1.4196 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9898 1.2800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0925 0.1999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2501 3.9225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4945 -1.3001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4541 4.2318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5629 0.8562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2265 -1.3001 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 25 1 0 0 0 0 10 28 1 0 0 0 0 11 26 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 33 1 0 0 0 0 15 29 2 0 0 0 0 16 30 2 0 0 0 0 16 33 1 0 0 0 0 17 22 1 0 0 0 0 17 31 1 1 0 0 0 18 25 1 0 0 0 0 18 28 1 1 0 0 0 19 26 1 1 0 0 0 19 27 1 0 0 0 0 20 26 1 1 0 0 0 20 28 1 0 0 0 0 21 27 1 1 0 0 0 21 34 1 0 0 0 0 22 15 1 6 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 1 0 0 0 24 32 2 0 0 0 0 24 34 1 0 0 0 0 26 5 1 1 0 0 0 27 6 1 1 0 0 0 28 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.3
Volume:	494.894
LogP:	3.721
LogD:	3.333
LogS:	-4.223
# Rotatable Bonds:	4
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.613
Synthetic Accessibility Score:	5.215
Fsp3:	0.893
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.853
MDCK Permeability:	1.9611507013905793e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.52
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.906
Plasma Protein Binding (PPB):	49.012969970703125%
Volume Distribution (VD):	0.756
Pgp-substrate:	49.70720291137695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.587
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.498
CYP3A4-substrate:	0.301

ADMET: Excretion

Clearance (CL):	6.351
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.517
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.181
Carcinogencity:	0.131
Eye Corrosion:	0.017
Eye Irritation:	0.027
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC67653

Natural Product ID:	NPC67653
*Common Name:**	VCWVASWFFYSLGB-QYBMFXCASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VCWVASWFFYSLGB-QYBMFXCASA-N
Standard InCHI:	InChI=1S/C28H42O6/c1-15(29)22-17(31)12-19-26(5)11-8-18-25(3,4)9-7-10-28(18,14-33-16(2)30)20(26)13-21-27(19,6)23(22)24(32)34-21/h17-23,31H,7-14H2,1-6H3/t17-,18-,19-,20-,21+,22+,23+,26-,27+,28+/m0/s1
SMILES:	CC(=O)[C@@H]1[C@H](C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(COC(=O)C)[C@H]3C[C@@H]3[C@]2(C)[C@H]1C(=O)O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508487
PubChem CID:	23245942
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33170	lendenfeldia chondrodes	Species	Thorectidae	Eukaryota	n.a.	palauan	n.a.	PMID[9917306]

☑ 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
EC50	1
Others	3

Activity Type	# Activity
Individual Protein	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3973	Individual Protein	Endothelial PAS domain-containing protein 1	Homo sapiens	EC50	>	100000.0	nM	PMID[523525]
NPT5842	Organism	Mytilus edulis	Mytilus edulis	Activity	=	90.0	%	PMID[523524]
NPT5842	Organism	Mytilus edulis	Mytilus edulis	Activity	=	100.0	%	PMID[523524]

☑ 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 NPC67653 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	407
0.1-0.2	3158
0.2-0.3	8273
0.3-0.4	13943
0.4-0.5	6444
0.5-0.6	5143
0.6-0.7	3874
0.7-0.8	1221
0.8-0.85	190
0.85-0.9	32
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471459
0.9412	High Similarity	NPC131104
0.9412	High Similarity	NPC3032
0.9412	High Similarity	NPC473319
0.9398	High Similarity	NPC219535
0.9398	High Similarity	NPC237938
0.9195	High Similarity	NPC475211
0.9195	High Similarity	NPC88337
0.9176	High Similarity	NPC83242
0.9167	High Similarity	NPC473299
0.8941	High Similarity	NPC477434
0.8941	High Similarity	NPC181871
0.8941	High Similarity	NPC9060
0.8837	High Similarity	NPC474572
0.8791	High Similarity	NPC62407
0.8791	High Similarity	NPC287354
0.8778	High Similarity	NPC476189
0.8721	High Similarity	NPC473336
0.8721	High Similarity	NPC471044
0.8652	High Similarity	NPC477443
0.8652	High Similarity	NPC477440
0.8652	High Similarity	NPC200580
0.8621	High Similarity	NPC62572
0.8556	High Similarity	NPC477444
0.8556	High Similarity	NPC477433
0.8556	High Similarity	NPC477442
0.8556	High Similarity	NPC185529
0.8556	High Similarity	NPC472146
0.8539	High Similarity	NPC236459
0.8523	High Similarity	NPC248216
0.8523	High Similarity	NPC120395
0.8506	High Similarity	NPC34984
0.8506	High Similarity	NPC25037
0.8495	Intermediate Similarity	NPC235109
0.8495	Intermediate Similarity	NPC163685
0.8488	Intermediate Similarity	NPC61107
0.8488	Intermediate Similarity	NPC289486
0.8462	Intermediate Similarity	NPC475878
0.8444	Intermediate Similarity	NPC61688
0.8427	Intermediate Similarity	NPC470920
0.8409	Intermediate Similarity	NPC473350
0.8404	Intermediate Similarity	NPC472145
0.8391	Intermediate Similarity	NPC15091
0.8387	Intermediate Similarity	NPC82633
0.8372	Intermediate Similarity	NPC476071
0.8372	Intermediate Similarity	NPC48756
0.8372	Intermediate Similarity	NPC50658
0.8372	Intermediate Similarity	NPC280781
0.8352	Intermediate Similarity	NPC50443
0.8352	Intermediate Similarity	NPC18536
0.8352	Intermediate Similarity	NPC77756
0.8333	Intermediate Similarity	NPC471221
0.8316	Intermediate Similarity	NPC471038
0.8316	Intermediate Similarity	NPC472144
0.8298	Intermediate Similarity	NPC193785
0.828	Intermediate Similarity	NPC247877
0.828	Intermediate Similarity	NPC309127
0.8261	Intermediate Similarity	NPC52756
0.8256	Intermediate Similarity	NPC125366
0.8235	Intermediate Similarity	NPC472608
0.8214	Intermediate Similarity	NPC474020
0.8202	Intermediate Similarity	NPC477205
0.8202	Intermediate Similarity	NPC477445
0.8172	Intermediate Similarity	NPC474379
0.8172	Intermediate Similarity	NPC161035
0.8161	Intermediate Similarity	NPC475743
0.8161	Intermediate Similarity	NPC474870
0.8161	Intermediate Similarity	NPC271572
0.8152	Intermediate Similarity	NPC470114
0.8144	Intermediate Similarity	NPC46848
0.814	Intermediate Similarity	NPC80891
0.814	Intermediate Similarity	NPC320144
0.814	Intermediate Similarity	NPC201276
0.8132	Intermediate Similarity	NPC226491
0.8132	Intermediate Similarity	NPC477614
0.8111	Intermediate Similarity	NPC476717
0.8111	Intermediate Similarity	NPC302111
0.8111	Intermediate Similarity	NPC477441
0.8105	Intermediate Similarity	NPC329910
0.8105	Intermediate Similarity	NPC475765
0.8105	Intermediate Similarity	NPC200054
0.8105	Intermediate Similarity	NPC116683
0.8105	Intermediate Similarity	NPC475785
0.8105	Intermediate Similarity	NPC29410
0.809	Intermediate Similarity	NPC50438
0.8085	Intermediate Similarity	NPC470424
0.8068	Intermediate Similarity	NPC30583
0.8068	Intermediate Similarity	NPC2096
0.8068	Intermediate Similarity	NPC208912
0.8061	Intermediate Similarity	NPC470172
0.8061	Intermediate Similarity	NPC275990
0.8046	Intermediate Similarity	NPC261616
0.8046	Intermediate Similarity	NPC134227
0.8041	Intermediate Similarity	NPC293866
0.8039	Intermediate Similarity	NPC470622
0.8023	Intermediate Similarity	NPC185465
0.8023	Intermediate Similarity	NPC80089
0.8023	Intermediate Similarity	NPC31031
0.8023	Intermediate Similarity	NPC224802
0.8023	Intermediate Similarity	NPC34046
0.8023	Intermediate Similarity	NPC171426
0.8023	Intermediate Similarity	NPC243594
0.8023	Intermediate Similarity	NPC324700
0.8022	Intermediate Similarity	NPC239938
0.8	Intermediate Similarity	NPC98639
0.8	Intermediate Similarity	NPC131350
0.8	Intermediate Similarity	NPC471046
0.8	Intermediate Similarity	NPC108840
0.8	Intermediate Similarity	NPC470232
0.8	Intermediate Similarity	NPC470229
0.8	Intermediate Similarity	NPC305808
0.798	Intermediate Similarity	NPC277074
0.798	Intermediate Similarity	NPC122811
0.798	Intermediate Similarity	NPC473406
0.798	Intermediate Similarity	NPC209298
0.798	Intermediate Similarity	NPC139347
0.798	Intermediate Similarity	NPC87927
0.7979	Intermediate Similarity	NPC472148
0.7979	Intermediate Similarity	NPC199543
0.7979	Intermediate Similarity	NPC472147
0.7979	Intermediate Similarity	NPC244356
0.7979	Intermediate Similarity	NPC224060
0.7978	Intermediate Similarity	NPC213737
0.7978	Intermediate Similarity	NPC474284
0.7978	Intermediate Similarity	NPC475820
0.7978	Intermediate Similarity	NPC474346
0.7978	Intermediate Similarity	NPC474253
0.7976	Intermediate Similarity	NPC55508
0.7959	Intermediate Similarity	NPC52899
0.7959	Intermediate Similarity	NPC163963
0.7959	Intermediate Similarity	NPC289148
0.7955	Intermediate Similarity	NPC58631
0.7955	Intermediate Similarity	NPC73515
0.7938	Intermediate Similarity	NPC20479
0.7938	Intermediate Similarity	NPC474793
0.7938	Intermediate Similarity	NPC38296
0.7938	Intermediate Similarity	NPC89099
0.7938	Intermediate Similarity	NPC162459
0.7938	Intermediate Similarity	NPC38471
0.7938	Intermediate Similarity	NPC98837
0.7938	Intermediate Similarity	NPC28864
0.7935	Intermediate Similarity	NPC476435
0.7931	Intermediate Similarity	NPC73013
0.7921	Intermediate Similarity	NPC201908
0.7921	Intermediate Similarity	NPC176949
0.7917	Intermediate Similarity	NPC256227
0.7912	Intermediate Similarity	NPC472272
0.7912	Intermediate Similarity	NPC80700
0.7907	Intermediate Similarity	NPC143133
0.7907	Intermediate Similarity	NPC298168
0.7907	Intermediate Similarity	NPC112463
0.7907	Intermediate Similarity	NPC207010
0.7907	Intermediate Similarity	NPC221420
0.7907	Intermediate Similarity	NPC317913
0.7907	Intermediate Similarity	NPC307865
0.7907	Intermediate Similarity	NPC143250
0.79	Intermediate Similarity	NPC98603
0.79	Intermediate Similarity	NPC327093
0.7895	Intermediate Similarity	NPC469982
0.7895	Intermediate Similarity	NPC475118
0.7895	Intermediate Similarity	NPC47853
0.7895	Intermediate Similarity	NPC470386
0.7895	Intermediate Similarity	NPC470385
0.7889	Intermediate Similarity	NPC475689
0.7889	Intermediate Similarity	NPC65133
0.7889	Intermediate Similarity	NPC319909
0.7889	Intermediate Similarity	NPC105895
0.7882	Intermediate Similarity	NPC159789
0.7882	Intermediate Similarity	NPC179858
0.7879	Intermediate Similarity	NPC80640
0.7879	Intermediate Similarity	NPC246736
0.7879	Intermediate Similarity	NPC214946
0.7879	Intermediate Similarity	NPC148628
0.7879	Intermediate Similarity	NPC471254
0.7879	Intermediate Similarity	NPC76866
0.7879	Intermediate Similarity	NPC286519
0.7879	Intermediate Similarity	NPC304832
0.7879	Intermediate Similarity	NPC88203
0.7872	Intermediate Similarity	NPC216137
0.7865	Intermediate Similarity	NPC268040
0.7865	Intermediate Similarity	NPC121121
0.7857	Intermediate Similarity	NPC470388
0.7857	Intermediate Similarity	NPC474755
0.7857	Intermediate Similarity	NPC287676
0.7857	Intermediate Similarity	NPC267921
0.7857	Intermediate Similarity	NPC80417
0.7849	Intermediate Similarity	NPC24705
0.7849	Intermediate Similarity	NPC56962
0.7841	Intermediate Similarity	NPC477851
0.7835	Intermediate Similarity	NPC472273
0.7835	Intermediate Similarity	NPC10864
0.7835	Intermediate Similarity	NPC471241
0.7835	Intermediate Similarity	NPC253586
0.7826	Intermediate Similarity	NPC252714
0.7826	Intermediate Similarity	NPC263802
0.7822	Intermediate Similarity	NPC37600
0.7822	Intermediate Similarity	NPC200957
0.7822	Intermediate Similarity	NPC138908
0.7822	Intermediate Similarity	NPC295366
0.7816	Intermediate Similarity	NPC475725

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 NPC67653 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	432
0.1-0.2	3417
0.2-0.3	3410
0.3-0.4	1151
0.4-0.5	354
0.5-0.6	230
0.6-0.7	130
0.7-0.8	19
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
0.8023	Intermediate Similarity	NPD6118	Approved
0.8023	Intermediate Similarity	NPD6697	Approved
0.8023	Intermediate Similarity	NPD6115	Approved
0.8023	Intermediate Similarity	NPD6114	Approved
0.7907	Intermediate Similarity	NPD6116	Phase 1
0.7882	Intermediate Similarity	NPD3703	Phase 2
0.7791	Intermediate Similarity	NPD6117	Approved
0.7684	Intermediate Similarity	NPD8034	Phase 2
0.7684	Intermediate Similarity	NPD8035	Phase 2
0.7558	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7902	Approved
0.7294	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5777	Approved
0.7117	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4245	Approved
0.7011	Intermediate Similarity	NPD4244	Approved
0.7	Intermediate Similarity	NPD7900	Approved
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7748	Approved
0.697	Remote Similarity	NPD7515	Phase 2
0.6944	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4224	Phase 2
0.6932	Remote Similarity	NPD6081	Approved
0.6923	Remote Similarity	NPD1700	Approved
0.69	Remote Similarity	NPD6399	Phase 3
0.6897	Remote Similarity	NPD8328	Phase 3
0.6897	Remote Similarity	NPD3698	Phase 2
0.6889	Remote Similarity	NPD3702	Approved
0.6882	Remote Similarity	NPD6928	Phase 2
0.6818	Remote Similarity	NPD4789	Approved
0.6789	Remote Similarity	NPD6373	Approved
0.6789	Remote Similarity	NPD6372	Approved
0.6782	Remote Similarity	NPD5360	Phase 3
0.6782	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD3671	Phase 1
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6628	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD229	Approved
0.6581	Remote Similarity	NPD6921	Approved
0.6555	Remote Similarity	NPD7492	Approved
0.6545	Remote Similarity	NPD6899	Approved
0.6545	Remote Similarity	NPD7320	Approved
0.6545	Remote Similarity	NPD6881	Approved
0.6542	Remote Similarity	NPD7632	Discontinued
0.6509	Remote Similarity	NPD8418	Phase 2
0.65	Remote Similarity	NPD6616	Approved
0.6496	Remote Similarity	NPD6054	Approved
0.6496	Remote Similarity	NPD6319	Approved
0.6496	Remote Similarity	NPD6059	Approved
0.6495	Remote Similarity	NPD3669	Approved
0.6495	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4802	Phase 2
0.6489	Remote Similarity	NPD4238	Approved
0.6458	Remote Similarity	NPD1780	Approved
0.6458	Remote Similarity	NPD1779	Approved
0.6455	Remote Similarity	NPD5697	Approved
0.6455	Remote Similarity	NPD5701	Approved
0.6446	Remote Similarity	NPD7078	Approved
0.6446	Remote Similarity	NPD8293	Discontinued
0.6436	Remote Similarity	NPD5328	Approved
0.6429	Remote Similarity	NPD7102	Approved
0.6429	Remote Similarity	NPD6883	Approved
0.6429	Remote Similarity	NPD7290	Approved
0.6429	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4632	Approved
0.6404	Remote Similarity	NPD8133	Approved
0.6396	Remote Similarity	NPD6011	Approved
0.6387	Remote Similarity	NPD6370	Approved
0.6381	Remote Similarity	NPD4697	Phase 3
0.6374	Remote Similarity	NPD4758	Discontinued
0.6372	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6869	Approved
0.6372	Remote Similarity	NPD6847	Approved
0.6372	Remote Similarity	NPD6617	Approved
0.6372	Remote Similarity	NPD8130	Phase 1
0.6341	Remote Similarity	NPD7319	Approved
0.6339	Remote Similarity	NPD6014	Approved
0.6339	Remote Similarity	NPD6012	Approved
0.6339	Remote Similarity	NPD6013	Approved
0.6339	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6882	Approved
0.6316	Remote Similarity	NPD5364	Discontinued
0.6316	Remote Similarity	NPD8297	Approved
0.6311	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD6079	Approved
0.6303	Remote Similarity	NPD6016	Approved
0.6303	Remote Similarity	NPD6015	Approved
0.63	Remote Similarity	NPD3618	Phase 1
0.6293	Remote Similarity	NPD6940	Discontinued
0.625	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD8171	Discontinued
0.6239	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD7115	Discovery
0.623	Remote Similarity	NPD7507	Approved
0.6198	Remote Similarity	NPD7604	Phase 2
0.6176	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4755	Approved
0.6167	Remote Similarity	NPD5983	Phase 2
0.6161	Remote Similarity	NPD6412	Phase 2
0.6161	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4634	Approved
0.6129	Remote Similarity	NPD6033	Approved
0.6117	Remote Similarity	NPD6101	Approved
0.6117	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4225	Approved
0.61	Remote Similarity	NPD4786	Approved
0.6098	Remote Similarity	NPD6336	Discontinued
0.6095	Remote Similarity	NPD5778	Approved
0.6095	Remote Similarity	NPD5779	Approved
0.6078	Remote Similarity	NPD3573	Approved
0.6075	Remote Similarity	NPD5221	Approved
0.6075	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5222	Approved
0.6061	Remote Similarity	NPD3667	Approved
0.6055	Remote Similarity	NPD4700	Approved
0.6055	Remote Similarity	NPD5286	Approved
0.6055	Remote Similarity	NPD5285	Approved
0.6055	Remote Similarity	NPD4696	Approved
0.605	Remote Similarity	NPD6335	Approved
0.6033	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6084	Phase 2
0.6019	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD5173	Approved
0.6017	Remote Similarity	NPD6274	Approved
0.6017	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD4788	Approved
0.5981	Remote Similarity	NPD7991	Discontinued
0.5981	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7334	Approved
0.598	Remote Similarity	NPD5330	Approved
0.598	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7146	Approved
0.598	Remote Similarity	NPD6409	Approved
0.598	Remote Similarity	NPD6684	Approved
0.598	Remote Similarity	NPD7521	Approved
0.5966	Remote Similarity	NPD6317	Approved
0.5965	Remote Similarity	NPD6686	Approved
0.5955	Remote Similarity	NPD7909	Approved
0.5946	Remote Similarity	NPD5211	Phase 2
0.5946	Remote Similarity	NPD4633	Approved
0.5946	Remote Similarity	NPD5224	Approved
0.5946	Remote Similarity	NPD5225	Approved
0.5946	Remote Similarity	NPD5226	Approved
0.5943	Remote Similarity	NPD4202	Approved
0.5929	Remote Similarity	NPD6920	Discontinued
0.5918	Remote Similarity	NPD7645	Phase 2
0.5917	Remote Similarity	NPD6314	Approved
0.5917	Remote Similarity	NPD6313	Approved
0.5914	Remote Similarity	NPD4787	Phase 1
0.5902	Remote Similarity	NPD8516	Approved
0.5902	Remote Similarity	NPD8517	Approved
0.5902	Remote Similarity	NPD6909	Approved
0.5902	Remote Similarity	NPD8515	Approved
0.5902	Remote Similarity	NPD8513	Phase 3
0.5902	Remote Similarity	NPD6908	Approved
0.5893	Remote Similarity	NPD5174	Approved
0.5893	Remote Similarity	NPD4754	Approved
0.5893	Remote Similarity	NPD5175	Approved
0.5865	Remote Similarity	NPD6672	Approved
0.5865	Remote Similarity	NPD5737	Approved
0.5865	Remote Similarity	NPD6903	Approved
0.5862	Remote Similarity	NPD3198	Approved
0.5859	Remote Similarity	NPD7525	Registered
0.5847	Remote Similarity	NPD8298	Phase 2
0.5841	Remote Similarity	NPD5141	Approved
0.5841	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5786	Approved
0.5818	Remote Similarity	NPD5696	Approved
0.581	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6067	Discontinued
0.5804	Remote Similarity	NPD8086	Approved
0.5804	Remote Similarity	NPD8082	Approved
0.5804	Remote Similarity	NPD8139	Approved
0.5804	Remote Similarity	NPD8084	Approved
0.5804	Remote Similarity	NPD8138	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