NPASS Compound

Structure

NPC474709 OpenBabel07101718292D 31 32 0 0 1 0 0 0 0 0999 V2000 -2.9111 -5.0173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6450 -6.2400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4132 -5.6505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2385 0.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9157 -2.3959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3396 -3.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2997 -3.6171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1860 -1.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8386 -1.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6772 -0.6947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2099 -3.1016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8386 0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5406 -4.1227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2499 -2.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4912 -1.1860 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8891 -4.3853 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6772 -0.9683 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.6947 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8946 -1.0653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5186 -5.2799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6772 -0.0000 0.0000 C 0 0 2 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 -3.1301 -3.3544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8492 -4.2589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5158 -1.4525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6629 -0.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5585 -5.4063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5613 0.7891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0210 -2.0254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5805 -3.9963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 5 30 1 0 0 0 0 6 7 1 0 0 0 0 6 15 2 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 12 15 1 0 0 0 0 12 31 1 0 0 0 0 13 22 1 0 0 0 0 13 23 1 0 0 0 0 14 24 2 0 0 0 0 14 31 1 0 0 0 0 16 15 1 6 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 6 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 23 1 1 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 28 1 0 0 0 0 22 4 1 6 0 0 0 23 11 1 1 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.26
Volume:	451.664
LogP:	0.865
LogD:	0.705
LogS:	-2.252
# Rotatable Bonds:	9
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	5.521
Fsp3:	0.826
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:	-4.96
MDCK Permeability:	0.0001591606269357726
Pgp-inhibitor:	0.249
Pgp-substrate:	0.894
Human Intestinal Absorption (HIA):	0.792
20% Bioavailability (F20%):	0.2
30% Bioavailability (F30%):	0.404

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	35.873931884765625%
Volume Distribution (VD):	0.643
Pgp-substrate:	63.36351013183594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.685
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.123
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.296
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	3.314
Half-life (T1/2):	0.514

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.291
Drug-inuced Liver Injury (DILI):	0.21
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.105
Carcinogencity:	0.708
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC474709

Natural Product ID:	NPC474709
*Common Name:**	Umbellacin I
IUPAC Name:	methyl (1S,4S,5R,6R,9R)-4-[(E)-1-acetyloxy-5,6-dihydroxy-6-methylhept-2-en-2-yl]-6,9-dihydroxy-1-methylbicyclo[4.3.1]decane-5-carboxylate
Synonyms:	Umbellacin I
Standard InCHIKey:	YFLWESDPLOQEEL-LTSMGGCUSA-N
Standard InCHI:	InChI=1S/C23H38O8/c1-14(24)31-12-15(6-7-17(25)21(2,3)28)16-8-10-22(4)13-23(29,11-9-18(22)26)19(16)20(27)30-5/h6,16-19,25-26,28-29H,7-13H2,1-5H3/b15-6-/t16-,17?,18-,19+,22+,23-/m1/s1
SMILES:	COC(=O)[C@@H]1[C@H](CC[C@]2(C[C@]1(O)CC[C@H]2O)C)/C(=CCC(C(O)(C)C)O)/COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479878
PubChem CID:	11697937
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic acids 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
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[12502332]
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562830]
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.6	ug ml-1	PMID[508055]

☑ 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 NPC474709 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	224
0.1-0.2	1359
0.2-0.3	4117
0.3-0.4	6794
0.4-0.5	14543
0.5-0.6	7606
0.6-0.7	6607
0.7-0.8	1418
0.8-0.85	24
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9579	High Similarity	NPC474718
0.9184	High Similarity	NPC478156
0.9	High Similarity	NPC239162
0.8842	High Similarity	NPC475972
0.88	High Similarity	NPC475091
0.8738	High Similarity	NPC94377
0.8654	High Similarity	NPC42662
0.8529	High Similarity	NPC69171
0.8529	High Similarity	NPC474165
0.844	Intermediate Similarity	NPC134430
0.844	Intermediate Similarity	NPC475809
0.8431	Intermediate Similarity	NPC183571
0.8411	Intermediate Similarity	NPC473877
0.84	Intermediate Similarity	NPC285513
0.8349	Intermediate Similarity	NPC474333
0.8333	Intermediate Similarity	NPC311592
0.8333	Intermediate Similarity	NPC75167
0.8302	Intermediate Similarity	NPC273433
0.8288	Intermediate Similarity	NPC473839
0.8288	Intermediate Similarity	NPC211093
0.8288	Intermediate Similarity	NPC77689
0.8288	Intermediate Similarity	NPC473636
0.8286	Intermediate Similarity	NPC112780
0.8273	Intermediate Similarity	NPC296822
0.8273	Intermediate Similarity	NPC476712
0.8273	Intermediate Similarity	NPC476713
0.8269	Intermediate Similarity	NPC475036
0.8257	Intermediate Similarity	NPC181145
0.8257	Intermediate Similarity	NPC73314
0.8241	Intermediate Similarity	NPC277769
0.8241	Intermediate Similarity	NPC4573
0.8218	Intermediate Similarity	NPC254496
0.8218	Intermediate Similarity	NPC474395
0.8214	Intermediate Similarity	NPC475003
0.8208	Intermediate Similarity	NPC151393
0.82	Intermediate Similarity	NPC471786
0.82	Intermediate Similarity	NPC37603
0.8182	Intermediate Similarity	NPC476711
0.8182	Intermediate Similarity	NPC476710
0.8173	Intermediate Similarity	NPC4620
0.8131	Intermediate Similarity	NPC475922
0.8125	Intermediate Similarity	NPC470186
0.8119	Intermediate Similarity	NPC11396
0.8119	Intermediate Similarity	NPC21302
0.8113	Intermediate Similarity	NPC67321
0.8113	Intermediate Similarity	NPC187435
0.8108	Intermediate Similarity	NPC475323
0.8108	Intermediate Similarity	NPC473656
0.8095	Intermediate Similarity	NPC220964
0.8095	Intermediate Similarity	NPC474550
0.8095	Intermediate Similarity	NPC473577
0.8095	Intermediate Similarity	NPC475585
0.8095	Intermediate Similarity	NPC475676
0.8077	Intermediate Similarity	NPC162973
0.8077	Intermediate Similarity	NPC476081
0.8073	Intermediate Similarity	NPC90952
0.8073	Intermediate Similarity	NPC269530
0.8073	Intermediate Similarity	NPC317687
0.8073	Intermediate Similarity	NPC174836
0.8056	Intermediate Similarity	NPC475134
0.8056	Intermediate Similarity	NPC83005
0.8056	Intermediate Similarity	NPC475563
0.8056	Intermediate Similarity	NPC161816
0.8056	Intermediate Similarity	NPC115257
0.8039	Intermediate Similarity	NPC134454
0.8039	Intermediate Similarity	NPC254121
0.8039	Intermediate Similarity	NPC17326
0.8036	Intermediate Similarity	NPC146280
0.8036	Intermediate Similarity	NPC124676
0.8034	Intermediate Similarity	NPC236999
0.802	Intermediate Similarity	NPC134067
0.8019	Intermediate Similarity	NPC179891
0.8019	Intermediate Similarity	NPC123726
0.8019	Intermediate Similarity	NPC475290
0.8019	Intermediate Similarity	NPC111952
0.8019	Intermediate Similarity	NPC284365
0.8018	Intermediate Similarity	NPC234858
0.8018	Intermediate Similarity	NPC154363
0.8018	Intermediate Similarity	NPC471127
0.8	Intermediate Similarity	NPC472399
0.8	Intermediate Similarity	NPC473802
0.8	Intermediate Similarity	NPC129992
0.8	Intermediate Similarity	NPC471204
0.8	Intermediate Similarity	NPC159533
0.8	Intermediate Similarity	NPC474775
0.7982	Intermediate Similarity	NPC317107
0.7982	Intermediate Similarity	NPC287311
0.7982	Intermediate Similarity	NPC475668
0.7982	Intermediate Similarity	NPC473921
0.7982	Intermediate Similarity	NPC475480
0.7981	Intermediate Similarity	NPC111292
0.7981	Intermediate Similarity	NPC11974
0.7981	Intermediate Similarity	NPC308824
0.7981	Intermediate Similarity	NPC471412
0.7963	Intermediate Similarity	NPC472216
0.7963	Intermediate Similarity	NPC218853
0.7963	Intermediate Similarity	NPC5475
0.7963	Intermediate Similarity	NPC284828
0.7963	Intermediate Similarity	NPC173905
0.7946	Intermediate Similarity	NPC10721
0.7946	Intermediate Similarity	NPC470775
0.7946	Intermediate Similarity	NPC473590
0.7946	Intermediate Similarity	NPC176513
0.7944	Intermediate Similarity	NPC324327
0.7944	Intermediate Similarity	NPC475510
0.7944	Intermediate Similarity	NPC72813
0.7944	Intermediate Similarity	NPC326994
0.7944	Intermediate Similarity	NPC194620
0.7944	Intermediate Similarity	NPC474421
0.7944	Intermediate Similarity	NPC143609
0.7944	Intermediate Similarity	NPC475587
0.7941	Intermediate Similarity	NPC472995
0.7941	Intermediate Similarity	NPC475304
0.7931	Intermediate Similarity	NPC473709
0.7931	Intermediate Similarity	NPC473919
0.7928	Intermediate Similarity	NPC474872
0.7928	Intermediate Similarity	NPC472400
0.7925	Intermediate Similarity	NPC118911
0.7925	Intermediate Similarity	NPC296950
0.7925	Intermediate Similarity	NPC203659
0.7925	Intermediate Similarity	NPC146731
0.7925	Intermediate Similarity	NPC258532
0.7921	Intermediate Similarity	NPC470958
0.7921	Intermediate Similarity	NPC470957
0.7917	Intermediate Similarity	NPC474776
0.7913	Intermediate Similarity	NPC257017
0.7913	Intermediate Similarity	NPC162009
0.7909	Intermediate Similarity	NPC475391
0.7909	Intermediate Similarity	NPC476801
0.7905	Intermediate Similarity	NPC472754
0.7905	Intermediate Similarity	NPC472552
0.7905	Intermediate Similarity	NPC165578
0.7905	Intermediate Similarity	NPC295791
0.7895	Intermediate Similarity	NPC145182
0.7895	Intermediate Similarity	NPC157252
0.7895	Intermediate Similarity	NPC471128
0.7895	Intermediate Similarity	NPC475885
0.7895	Intermediate Similarity	NPC471126
0.7895	Intermediate Similarity	NPC48692
0.7895	Intermediate Similarity	NPC472004
0.789	Intermediate Similarity	NPC477103
0.789	Intermediate Similarity	NPC473594
0.789	Intermediate Similarity	NPC473843
0.789	Intermediate Similarity	NPC119550
0.789	Intermediate Similarity	NPC474586
0.789	Intermediate Similarity	NPC473975
0.789	Intermediate Similarity	NPC472214
0.789	Intermediate Similarity	NPC472215
0.789	Intermediate Similarity	NPC250956
0.7885	Intermediate Similarity	NPC471413
0.7885	Intermediate Similarity	NPC272223
0.7876	Intermediate Similarity	NPC251310
0.7876	Intermediate Similarity	NPC475372
0.787	Intermediate Similarity	NPC474664
0.787	Intermediate Similarity	NPC14862
0.787	Intermediate Similarity	NPC472219
0.787	Intermediate Similarity	NPC476479
0.787	Intermediate Similarity	NPC233379
0.787	Intermediate Similarity	NPC327286
0.787	Intermediate Similarity	NPC473595
0.787	Intermediate Similarity	NPC472217
0.787	Intermediate Similarity	NPC322903
0.787	Intermediate Similarity	NPC469916
0.787	Intermediate Similarity	NPC306265
0.787	Intermediate Similarity	NPC473939
0.787	Intermediate Similarity	NPC55972
0.787	Intermediate Similarity	NPC472439
0.787	Intermediate Similarity	NPC169888
0.787	Intermediate Similarity	NPC89171
0.787	Intermediate Similarity	NPC472218
0.787	Intermediate Similarity	NPC308191
0.787	Intermediate Similarity	NPC476802
0.7864	Intermediate Similarity	NPC473244
0.7864	Intermediate Similarity	NPC474977
0.7864	Intermediate Similarity	NPC40812
0.7863	Intermediate Similarity	NPC471939
0.7857	Intermediate Similarity	NPC474765
0.7857	Intermediate Similarity	NPC471816
0.785	Intermediate Similarity	NPC127609
0.785	Intermediate Similarity	NPC60315
0.785	Intermediate Similarity	NPC470975
0.785	Intermediate Similarity	NPC470979
0.785	Intermediate Similarity	NPC16313
0.785	Intermediate Similarity	NPC9303
0.785	Intermediate Similarity	NPC103088
0.7845	Intermediate Similarity	NPC469352
0.7845	Intermediate Similarity	NPC67251
0.7843	Intermediate Similarity	NPC292178
0.7843	Intermediate Similarity	NPC266899
0.7843	Intermediate Similarity	NPC86893
0.7843	Intermediate Similarity	NPC36954
0.7838	Intermediate Similarity	NPC472757
0.7838	Intermediate Similarity	NPC478212
0.7838	Intermediate Similarity	NPC208998
0.7838	Intermediate Similarity	NPC71889
0.7838	Intermediate Similarity	NPC474937
0.7838	Intermediate Similarity	NPC7921
0.7838	Intermediate Similarity	NPC159333
0.7838	Intermediate Similarity	NPC477126
0.783	Intermediate Similarity	NPC475945

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 NPC474709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1799
0.2-0.3	3548
0.3-0.4	2236
0.4-0.5	911
0.5-0.6	319
0.6-0.7	128
0.7-0.8	12
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
0.78	Intermediate Similarity	NPD46	Approved
0.78	Intermediate Similarity	NPD6698	Approved
0.7727	Intermediate Similarity	NPD6371	Approved
0.7723	Intermediate Similarity	NPD7983	Approved
0.7706	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4225	Approved
0.7615	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6686	Approved
0.7477	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD5344	Discontinued
0.7476	Intermediate Similarity	NPD5779	Approved
0.7476	Intermediate Similarity	NPD5778	Approved
0.7453	Intermediate Similarity	NPD7638	Approved
0.7383	Intermediate Similarity	NPD7640	Approved
0.7383	Intermediate Similarity	NPD7639	Approved
0.7377	Intermediate Similarity	NPD7319	Approved
0.7333	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD7507	Approved
0.7257	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD8516	Approved
0.7227	Intermediate Similarity	NPD8513	Phase 3
0.7227	Intermediate Similarity	NPD8515	Approved
0.7227	Intermediate Similarity	NPD8517	Approved
0.7212	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD6319	Approved
0.7115	Intermediate Similarity	NPD7838	Discovery
0.7083	Intermediate Similarity	NPD6921	Approved
0.7064	Intermediate Similarity	NPD6648	Approved
0.7034	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6101	Approved
0.7019	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6053	Discontinued
0.6975	Remote Similarity	NPD7328	Approved
0.6975	Remote Similarity	NPD7327	Approved
0.6967	Remote Similarity	NPD8328	Phase 3
0.6944	Remote Similarity	NPD7839	Suspended
0.6935	Remote Similarity	NPD8074	Phase 3
0.6923	Remote Similarity	NPD8133	Approved
0.6917	Remote Similarity	NPD7516	Approved
0.6903	Remote Similarity	NPD7128	Approved
0.6903	Remote Similarity	NPD6675	Approved
0.6903	Remote Similarity	NPD5739	Approved
0.6903	Remote Similarity	NPD6402	Approved
0.6897	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7637	Suspended
0.687	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6373	Approved
0.687	Remote Similarity	NPD6372	Approved
0.6838	Remote Similarity	NPD8297	Approved
0.6822	Remote Similarity	NPD6399	Phase 3
0.6803	Remote Similarity	NPD8033	Approved
0.6792	Remote Similarity	NPD5785	Approved
0.6786	Remote Similarity	NPD7632	Discontinued
0.6783	Remote Similarity	NPD7320	Approved
0.6783	Remote Similarity	NPD6899	Approved
0.6783	Remote Similarity	NPD6881	Approved
0.678	Remote Similarity	NPD4632	Approved
0.6774	Remote Similarity	NPD7492	Approved
0.6759	Remote Similarity	NPD5282	Discontinued
0.6759	Remote Similarity	NPD7748	Approved
0.6752	Remote Similarity	NPD6649	Approved
0.6752	Remote Similarity	NPD6650	Approved
0.6729	Remote Similarity	NPD7515	Phase 2
0.6727	Remote Similarity	NPD7902	Approved
0.6721	Remote Similarity	NPD6054	Approved
0.6721	Remote Similarity	NPD8377	Approved
0.6721	Remote Similarity	NPD8294	Approved
0.6721	Remote Similarity	NPD6059	Approved
0.672	Remote Similarity	NPD8273	Phase 1
0.672	Remote Similarity	NPD6616	Approved
0.6698	Remote Similarity	NPD1695	Approved
0.6696	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD5697	Approved
0.6695	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD8378	Approved
0.6614	Remote Similarity	NPD7736	Approved
0.6613	Remote Similarity	NPD6370	Approved
0.661	Remote Similarity	NPD6869	Approved
0.661	Remote Similarity	NPD6617	Approved
0.661	Remote Similarity	NPD8130	Phase 1
0.661	Remote Similarity	NPD6847	Approved
0.6609	Remote Similarity	NPD6008	Approved
0.6602	Remote Similarity	NPD7154	Phase 3
0.6581	Remote Similarity	NPD6013	Approved
0.6581	Remote Similarity	NPD6014	Approved
0.6581	Remote Similarity	NPD6012	Approved
0.6571	Remote Similarity	NPD5786	Approved
0.6569	Remote Similarity	NPD5369	Approved
0.6552	Remote Similarity	NPD6412	Phase 2
0.6532	Remote Similarity	NPD6015	Approved
0.6532	Remote Similarity	NPD7503	Approved
0.6532	Remote Similarity	NPD6016	Approved
0.6509	Remote Similarity	NPD4250	Approved
0.6509	Remote Similarity	NPD4251	Approved
0.6505	Remote Similarity	NPD6435	Approved
0.6505	Remote Similarity	NPD4269	Approved
0.6505	Remote Similarity	NPD4270	Approved
0.6496	Remote Similarity	NPD6011	Approved
0.648	Remote Similarity	NPD5988	Approved
0.6476	Remote Similarity	NPD1694	Approved
0.6476	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6009	Approved
0.6471	Remote Similarity	NPD4821	Approved
0.6471	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4820	Approved
0.6471	Remote Similarity	NPD4822	Approved
0.6471	Remote Similarity	NPD4819	Approved
0.6457	Remote Similarity	NPD8451	Approved
0.6455	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7900	Approved
0.6442	Remote Similarity	NPD5362	Discontinued
0.6436	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4755	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6422	Remote Similarity	NPD8035	Phase 2
0.6422	Remote Similarity	NPD8034	Phase 2
0.6415	Remote Similarity	NPD4249	Approved
0.6406	Remote Similarity	NPD8448	Approved
0.64	Remote Similarity	NPD5983	Phase 2
0.64	Remote Similarity	NPD8444	Approved
0.6389	Remote Similarity	NPD5328	Approved
0.6387	Remote Similarity	NPD6421	Discontinued
0.6381	Remote Similarity	NPD4786	Approved
0.6381	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7524	Approved
0.6348	Remote Similarity	NPD5211	Phase 2
0.6346	Remote Similarity	NPD3667	Approved
0.6328	Remote Similarity	NPD6336	Discontinued
0.6321	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5363	Approved
0.6316	Remote Similarity	NPD4700	Approved
0.6316	Remote Similarity	NPD5286	Approved
0.6316	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD4696	Approved
0.6311	Remote Similarity	NPD5368	Approved
0.6311	Remote Similarity	NPD4252	Approved
0.63	Remote Similarity	NPD8039	Approved
0.6299	Remote Similarity	NPD7830	Approved
0.6299	Remote Similarity	NPD7642	Approved
0.6299	Remote Similarity	NPD7829	Approved
0.6286	Remote Similarity	NPD6695	Phase 3
0.6275	Remote Similarity	NPD4268	Approved
0.6275	Remote Similarity	NPD4271	Approved
0.6273	Remote Similarity	NPD6079	Approved
0.6269	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD3618	Phase 1
0.626	Remote Similarity	NPD8390	Approved
0.626	Remote Similarity	NPD6274	Approved
0.626	Remote Similarity	NPD8392	Approved
0.626	Remote Similarity	NPD8391	Approved
0.625	Remote Similarity	NPD8299	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD8342	Approved
0.625	Remote Similarity	NPD8341	Approved
0.625	Remote Similarity	NPD8340	Approved
0.624	Remote Similarity	NPD7100	Approved
0.624	Remote Similarity	NPD7101	Approved
0.6239	Remote Similarity	NPD5141	Approved
0.6231	Remote Similarity	NPD6033	Approved
0.6222	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4202	Approved
0.6212	Remote Similarity	NPD7260	Phase 2
0.6207	Remote Similarity	NPD5225	Approved
0.6207	Remote Similarity	NPD4633	Approved
0.6207	Remote Similarity	NPD5226	Approved
0.6207	Remote Similarity	NPD5224	Approved
0.6204	Remote Similarity	NPD3573	Approved
0.6194	Remote Similarity	NPD8415	Approved
0.6186	Remote Similarity	NPD4768	Approved
0.6186	Remote Similarity	NPD4767	Approved
0.6182	Remote Similarity	NPD3168	Discontinued
0.616	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD7525	Registered
0.6154	Remote Similarity	NPD5175	Approved
0.6154	Remote Similarity	NPD5174	Approved
0.6142	Remote Similarity	NPD6908	Approved
0.6142	Remote Similarity	NPD6909	Approved
0.6121	Remote Similarity	NPD5223	Approved
0.6111	Remote Similarity	NPD6409	Approved
0.6111	Remote Similarity	NPD7146	Approved
0.6111	Remote Similarity	NPD7334	Approved
0.6111	Remote Similarity	NPD6422	Discontinued

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