NPASS Compound

Structure

NPC117604 OpenBabel07101719242D 26 29 0 0 1 0 0 0 0 0999 V2000 6.5320 -2.1500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7237 0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0741 -2.9651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3402 0.5010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6206 -0.4589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4149 0.8802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0450 -1.2766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5415 0.3932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0686 -2.8605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5686 -1.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0468 -1.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5468 -2.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7378 -3.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3776 -0.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5298 -4.5818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8200 0.3036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6513 -3.1970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 9 2 0 0 0 0 2 10 1 0 0 0 0 4 12 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 11 3 1 6 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 19 1 1 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	362.446
LogP:	3.001
LogD:	2.003
LogS:	-4.261
# Rotatable Bonds:	3
TPSA:	85.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.459
Synthetic Accessibility Score:	5.234
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.028
MDCK Permeability:	3.8694084651069716e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.812
Plasma Protein Binding (PPB):	66.05310821533203%
Volume Distribution (VD):	1.354
Pgp-substrate:	40.61424255371094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.138
CYP1A2-substrate:	0.576
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.692
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.449
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	6.423
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.866
AMES Toxicity:	0.464
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.107
Skin Sensitization:	0.173
Carcinogencity:	0.143
Eye Corrosion:	0.007
Eye Irritation:	0.04
Respiratory Toxicity:	0.337

Download Data

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

Natural Product: NPC117604

Natural Product ID:	NPC117604
*Common Name:**	8Alpha-(2'r,3'r-Epoxy-2'-Methylbutyryloxy)-9Alpha-Hydroxymontahibisciolide
IUPAC Name:	[(3R,3aS,4R,4aR,9aS,9bR)-4a-hydroxy-3,5-dimethyl-9-methylidene-2-oxo-3a,4,7,8,9a,9b-hexahydro-3H-azuleno[1,2-b]furan-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
Synonyms:
Standard InCHIKey:	SBZMGZYHKNGAQP-AFXNQAGISA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-9-7-6-8-10(2)20(23)14(9)15-13(11(3)17(21)24-15)16(20)25-18(22)19(5)12(4)26-19/h8,11-16,23H,1,6-7H2,2-5H3/t11-,12-,13+,14+,15-,16-,19-,20+/m1/s1
SMILES:	C=C1CCC=C([C@@]2([C@@H]1[C@@H]1OC(=O)[C@@H]([C@@H]1[C@H]2OC(=O)[C@]1(C)O[C@@H]1C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL377092
PubChem CID:	21577295
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO12991	Montanoa hibiscifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104492]
NPO12991	Montanoa hibiscifolia	Species	Asteraceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	200.0	uM	PMID[464504]
NPT2	Others	Unspecified		Activity	=	200.0	uM	PMID[464505]

☑ 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 NPC117604 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	265
0.1-0.2	1660
0.2-0.3	5822
0.3-0.4	13288
0.4-0.5	11372
0.5-0.6	6699
0.6-0.7	3002
0.7-0.8	545
0.8-0.85	42
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8491	Intermediate Similarity	NPC54737
0.8468	Intermediate Similarity	NPC54739
0.8447	Intermediate Similarity	NPC221615
0.8407	Intermediate Similarity	NPC477092
0.8365	Intermediate Similarity	NPC186861
0.8319	Intermediate Similarity	NPC475401
0.8318	Intermediate Similarity	NPC44004
0.8318	Intermediate Similarity	NPC243998
0.8318	Intermediate Similarity	NPC223450
0.8317	Intermediate Similarity	NPC475788
0.8302	Intermediate Similarity	NPC124881
0.8286	Intermediate Similarity	NPC150923
0.8257	Intermediate Similarity	NPC59489
0.8257	Intermediate Similarity	NPC139838
0.8252	Intermediate Similarity	NPC213078
0.823	Intermediate Similarity	NPC475305
0.8224	Intermediate Similarity	NPC474741
0.8224	Intermediate Similarity	NPC100487
0.819	Intermediate Similarity	NPC471381
0.8173	Intermediate Similarity	NPC161493
0.8155	Intermediate Similarity	NPC67584
0.8148	Intermediate Similarity	NPC314244
0.8108	Intermediate Similarity	NPC475495
0.8073	Intermediate Similarity	NPC26617
0.8058	Intermediate Similarity	NPC127019
0.8037	Intermediate Similarity	NPC49393
0.8037	Intermediate Similarity	NPC105725
0.8036	Intermediate Similarity	NPC475277
0.8036	Intermediate Similarity	NPC477093
0.8036	Intermediate Similarity	NPC473522
0.8	Intermediate Similarity	NPC474313
0.8	Intermediate Similarity	NPC471150
0.7981	Intermediate Similarity	NPC270013
0.7981	Intermediate Similarity	NPC213698
0.7981	Intermediate Similarity	NPC14961
0.7981	Intermediate Similarity	NPC170120
0.7981	Intermediate Similarity	NPC52044
0.7981	Intermediate Similarity	NPC476053
0.7963	Intermediate Similarity	NPC475945
0.7963	Intermediate Similarity	NPC475871
0.7946	Intermediate Similarity	NPC287311
0.7944	Intermediate Similarity	NPC474339
0.7944	Intermediate Similarity	NPC471767
0.7944	Intermediate Similarity	NPC474742
0.7944	Intermediate Similarity	NPC164598
0.7925	Intermediate Similarity	NPC45125
0.7913	Intermediate Similarity	NPC471146
0.7909	Intermediate Similarity	NPC477513
0.7885	Intermediate Similarity	NPC474035
0.7885	Intermediate Similarity	NPC81386
0.787	Intermediate Similarity	NPC471757
0.787	Intermediate Similarity	NPC118405
0.787	Intermediate Similarity	NPC78127
0.787	Intermediate Similarity	NPC474747
0.787	Intermediate Similarity	NPC250594
0.787	Intermediate Similarity	NPC471148
0.7864	Intermediate Similarity	NPC469627
0.785	Intermediate Similarity	NPC288876
0.785	Intermediate Similarity	NPC475949
0.785	Intermediate Similarity	NPC70865
0.7838	Intermediate Similarity	NPC233379
0.7838	Intermediate Similarity	NPC14862
0.7838	Intermediate Similarity	NPC308191
0.7838	Intermediate Similarity	NPC474664
0.7826	Intermediate Similarity	NPC255450
0.7826	Intermediate Similarity	NPC170692
0.7818	Intermediate Similarity	NPC16313
0.7818	Intermediate Similarity	NPC190867
0.7818	Intermediate Similarity	NPC475802
0.7818	Intermediate Similarity	NPC9303
0.7818	Intermediate Similarity	NPC179891
0.781	Intermediate Similarity	NPC472873
0.781	Intermediate Similarity	NPC475659
0.781	Intermediate Similarity	NPC163228
0.7788	Intermediate Similarity	NPC475912
0.7788	Intermediate Similarity	NPC258216
0.7788	Intermediate Similarity	NPC212486
0.7778	Intermediate Similarity	NPC133907
0.7778	Intermediate Similarity	NPC201718
0.7778	Intermediate Similarity	NPC46998
0.7778	Intermediate Similarity	NPC110443
0.7778	Intermediate Similarity	NPC128733
0.7778	Intermediate Similarity	NPC476270
0.7778	Intermediate Similarity	NPC185141
0.7768	Intermediate Similarity	NPC15218
0.7767	Intermediate Similarity	NPC37607
0.7767	Intermediate Similarity	NPC301969
0.7767	Intermediate Similarity	NPC65359
0.7759	Intermediate Similarity	NPC471145
0.7757	Intermediate Similarity	NPC109556
0.7757	Intermediate Similarity	NPC470188
0.7757	Intermediate Similarity	NPC470541
0.7748	Intermediate Similarity	NPC324327
0.7748	Intermediate Similarity	NPC326994
0.7748	Intermediate Similarity	NPC194620
0.7748	Intermediate Similarity	NPC72813
0.7748	Intermediate Similarity	NPC204884
0.7748	Intermediate Similarity	NPC474421
0.7745	Intermediate Similarity	NPC53158
0.7739	Intermediate Similarity	NPC121816
0.7736	Intermediate Similarity	NPC476315
0.7736	Intermediate Similarity	NPC473859
0.7719	Intermediate Similarity	NPC126691
0.7714	Intermediate Similarity	NPC470010
0.7714	Intermediate Similarity	NPC323008
0.7714	Intermediate Similarity	NPC262133
0.7714	Intermediate Similarity	NPC470013
0.7714	Intermediate Similarity	NPC198853
0.7706	Intermediate Similarity	NPC86077
0.7706	Intermediate Similarity	NPC149371
0.7705	Intermediate Similarity	NPC172823
0.7699	Intermediate Similarity	NPC477103
0.7699	Intermediate Similarity	NPC161816
0.7699	Intermediate Similarity	NPC257240
0.7699	Intermediate Similarity	NPC115257
0.7692	Intermediate Similarity	NPC20713
0.7692	Intermediate Similarity	NPC155215
0.7679	Intermediate Similarity	NPC327286
0.7679	Intermediate Similarity	NPC55972
0.7679	Intermediate Similarity	NPC169888
0.7672	Intermediate Similarity	NPC277583
0.7664	Intermediate Similarity	NPC181151
0.7658	Intermediate Similarity	NPC473488
0.7658	Intermediate Similarity	NPC474101
0.7658	Intermediate Similarity	NPC475661
0.7652	Intermediate Similarity	NPC273242
0.7647	Intermediate Similarity	NPC179659
0.7642	Intermediate Similarity	NPC475900
0.7642	Intermediate Similarity	NPC36954
0.7642	Intermediate Similarity	NPC13071
0.7642	Intermediate Similarity	NPC224689
0.7636	Intermediate Similarity	NPC475873
0.7636	Intermediate Similarity	NPC474775
0.7636	Intermediate Similarity	NPC472755
0.7619	Intermediate Similarity	NPC179746
0.7619	Intermediate Similarity	NPC476300
0.7619	Intermediate Similarity	NPC81419
0.7615	Intermediate Similarity	NPC472753
0.7615	Intermediate Similarity	NPC171759
0.7615	Intermediate Similarity	NPC477511
0.7615	Intermediate Similarity	NPC47880
0.7615	Intermediate Similarity	NPC477950
0.7615	Intermediate Similarity	NPC477356
0.7615	Intermediate Similarity	NPC264477
0.7611	Intermediate Similarity	NPC471400
0.7611	Intermediate Similarity	NPC475922
0.7611	Intermediate Similarity	NPC477102
0.7611	Intermediate Similarity	NPC38154
0.7596	Intermediate Similarity	NPC246173
0.7596	Intermediate Similarity	NPC51004
0.7593	Intermediate Similarity	NPC473326
0.7593	Intermediate Similarity	NPC477355
0.7593	Intermediate Similarity	NPC471144
0.7589	Intermediate Similarity	NPC470192
0.7581	Intermediate Similarity	NPC469351
0.7581	Intermediate Similarity	NPC475389
0.7581	Intermediate Similarity	NPC473838
0.7573	Intermediate Similarity	NPC224652
0.757	Intermediate Similarity	NPC476009
0.757	Intermediate Similarity	NPC17585
0.7568	Intermediate Similarity	NPC475676
0.7568	Intermediate Similarity	NPC220964
0.7568	Intermediate Similarity	NPC203659
0.7565	Intermediate Similarity	NPC189338
0.7565	Intermediate Similarity	NPC95290
0.7565	Intermediate Similarity	NPC471933
0.7565	Intermediate Similarity	NPC35069
0.7565	Intermediate Similarity	NPC258711
0.7549	Intermediate Similarity	NPC469626
0.7549	Intermediate Similarity	NPC475491
0.7547	Intermediate Similarity	NPC477131
0.7547	Intermediate Similarity	NPC57405
0.7547	Intermediate Similarity	NPC303942
0.7545	Intermediate Similarity	NPC472754
0.7545	Intermediate Similarity	NPC70369
0.7544	Intermediate Similarity	NPC99760
0.7544	Intermediate Similarity	NPC41551
0.7544	Intermediate Similarity	NPC50223
0.7542	Intermediate Similarity	NPC475130
0.7542	Intermediate Similarity	NPC474286
0.754	Intermediate Similarity	NPC471234
0.7524	Intermediate Similarity	NPC30515
0.7524	Intermediate Similarity	NPC133698
0.7524	Intermediate Similarity	NPC12172
0.7524	Intermediate Similarity	NPC144629
0.7524	Intermediate Similarity	NPC184463
0.7524	Intermediate Similarity	NPC208886
0.7524	Intermediate Similarity	NPC184063
0.7524	Intermediate Similarity	NPC476705
0.7524	Intermediate Similarity	NPC475925
0.7523	Intermediate Similarity	NPC280963
0.7521	Intermediate Similarity	NPC42747
0.75	Intermediate Similarity	NPC470880
0.75	Intermediate Similarity	NPC106395
0.75	Intermediate Similarity	NPC213947
0.75	Intermediate Similarity	NPC291643
0.75	Intermediate Similarity	NPC87090
0.75	Intermediate Similarity	NPC108475
0.75	Intermediate Similarity	NPC307411
0.75	Intermediate Similarity	NPC46269

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 NPC117604 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	2330
0.2-0.3	3888
0.3-0.4	1847
0.4-0.5	492
0.5-0.6	242
0.6-0.7	90
0.7-0.8	6
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
0.8073	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD6371	Approved
0.7379	Intermediate Similarity	NPD4249	Approved
0.7358	Intermediate Similarity	NPD7983	Approved
0.7333	Intermediate Similarity	NPD1695	Approved
0.7308	Intermediate Similarity	NPD4250	Approved
0.7308	Intermediate Similarity	NPD4251	Approved
0.7212	Intermediate Similarity	NPD5786	Approved
0.7131	Intermediate Similarity	NPD6319	Approved
0.7119	Intermediate Similarity	NPD6053	Discontinued
0.7087	Intermediate Similarity	NPD5362	Discontinued
0.704	Intermediate Similarity	NPD7492	Approved
0.6992	Remote Similarity	NPD6054	Approved
0.6992	Remote Similarity	NPD6059	Approved
0.699	Remote Similarity	NPD6435	Approved
0.699	Remote Similarity	NPD4270	Approved
0.699	Remote Similarity	NPD4269	Approved
0.6984	Remote Similarity	NPD6616	Approved
0.6961	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4819	Approved
0.6961	Remote Similarity	NPD4822	Approved
0.6961	Remote Similarity	NPD4821	Approved
0.6961	Remote Similarity	NPD4820	Approved
0.6952	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6698	Approved
0.6944	Remote Similarity	NPD46	Approved
0.6935	Remote Similarity	NPD6016	Approved
0.6935	Remote Similarity	NPD6015	Approved
0.6929	Remote Similarity	NPD8293	Discontinued
0.6929	Remote Similarity	NPD7078	Approved
0.6909	Remote Similarity	NPD5282	Discontinued
0.6897	Remote Similarity	NPD6008	Approved
0.6893	Remote Similarity	NPD5369	Approved
0.688	Remote Similarity	NPD6370	Approved
0.688	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD7736	Approved
0.6847	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1700	Approved
0.6818	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5779	Approved
0.681	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5368	Approved
0.6796	Remote Similarity	NPD4252	Approved
0.6792	Remote Similarity	NPD5363	Approved
0.6765	Remote Similarity	NPD4271	Approved
0.6765	Remote Similarity	NPD4268	Approved
0.6762	Remote Similarity	NPD7154	Phase 3
0.675	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4632	Approved
0.6639	Remote Similarity	NPD7320	Approved
0.6636	Remote Similarity	NPD5785	Approved
0.6636	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7115	Discovery
0.661	Remote Similarity	NPD6675	Approved
0.661	Remote Similarity	NPD5739	Approved
0.661	Remote Similarity	NPD6402	Approved
0.661	Remote Similarity	NPD7128	Approved
0.6604	Remote Similarity	NPD5332	Approved
0.6604	Remote Similarity	NPD5331	Approved
0.6583	Remote Similarity	NPD6372	Approved
0.6583	Remote Similarity	NPD6373	Approved
0.6571	Remote Similarity	NPD4790	Discontinued
0.6565	Remote Similarity	NPD7319	Approved
0.6557	Remote Similarity	NPD8297	Approved
0.6555	Remote Similarity	NPD5701	Approved
0.6555	Remote Similarity	NPD5697	Approved
0.6549	Remote Similarity	NPD5695	Phase 3
0.6535	Remote Similarity	NPD8516	Approved
0.6535	Remote Similarity	NPD8517	Approved
0.6535	Remote Similarity	NPD8515	Approved
0.6535	Remote Similarity	NPD8513	Phase 3
0.6529	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD5696	Approved
0.65	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD6881	Approved
0.6489	Remote Similarity	NPD6033	Approved
0.6486	Remote Similarity	NPD7838	Discovery
0.648	Remote Similarity	NPD6009	Approved
0.6475	Remote Similarity	NPD6650	Approved
0.6475	Remote Similarity	NPD6649	Approved
0.6462	Remote Similarity	NPD7507	Approved
0.6446	Remote Similarity	NPD6013	Approved
0.6446	Remote Similarity	NPD6014	Approved
0.6446	Remote Similarity	NPD6012	Approved
0.6435	Remote Similarity	NPD6084	Phase 2
0.6435	Remote Similarity	NPD6083	Phase 2
0.6434	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD7637	Suspended
0.6406	Remote Similarity	NPD5983	Phase 2
0.6393	Remote Similarity	NPD7102	Approved
0.6393	Remote Similarity	NPD7290	Approved
0.6393	Remote Similarity	NPD6883	Approved
0.6379	Remote Similarity	NPD4225	Approved
0.6364	Remote Similarity	NPD6011	Approved
0.6355	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7839	Suspended
0.6341	Remote Similarity	NPD6847	Approved
0.6341	Remote Similarity	NPD6869	Approved
0.6341	Remote Similarity	NPD6617	Approved
0.6341	Remote Similarity	NPD8130	Phase 1
0.629	Remote Similarity	NPD6882	Approved
0.6288	Remote Similarity	NPD8074	Phase 3
0.6286	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5344	Discontinued
0.6269	Remote Similarity	NPD5956	Approved
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6399	Phase 3
0.6218	Remote Similarity	NPD5211	Phase 2
0.6212	Remote Similarity	NPD6336	Discontinued
0.621	Remote Similarity	NPD2204	Approved
0.621	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4755	Approved
0.6148	Remote Similarity	NPD6412	Phase 2
0.6147	Remote Similarity	NPD6110	Phase 1
0.6142	Remote Similarity	NPD6274	Approved
0.614	Remote Similarity	NPD6411	Approved
0.6116	Remote Similarity	NPD5141	Approved
0.6115	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6686	Approved
0.6094	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.609	Remote Similarity	NPD8273	Phase 1
0.6071	Remote Similarity	NPD7524	Approved
0.6068	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD8328	Phase 3
0.605	Remote Similarity	NPD7639	Approved
0.605	Remote Similarity	NPD4700	Approved
0.605	Remote Similarity	NPD5285	Approved
0.605	Remote Similarity	NPD5286	Approved
0.605	Remote Similarity	NPD4696	Approved
0.605	Remote Similarity	NPD7640	Approved
0.605	Remote Similarity	NPD6648	Approved
0.6048	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD8033	Approved
0.6031	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD8342	Approved
0.6015	Remote Similarity	NPD8341	Approved
0.6015	Remote Similarity	NPD8340	Approved
0.6015	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5693	Phase 1
0.5983	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6098	Approved
0.5969	Remote Similarity	NPD6317	Approved
0.5966	Remote Similarity	NPD7638	Approved
0.5966	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5370	Suspended
0.5965	Remote Similarity	NPD6673	Approved
0.5965	Remote Similarity	NPD6904	Approved
0.5965	Remote Similarity	NPD6080	Approved
0.5965	Remote Similarity	NPD4753	Phase 2
0.595	Remote Similarity	NPD5225	Approved
0.595	Remote Similarity	NPD5226	Approved
0.595	Remote Similarity	NPD4633	Approved
0.595	Remote Similarity	NPD5224	Approved
0.5946	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.594	Remote Similarity	NPD7642	Approved
0.5923	Remote Similarity	NPD6335	Approved
0.5923	Remote Similarity	NPD6314	Approved
0.5923	Remote Similarity	NPD7327	Approved
0.5923	Remote Similarity	NPD6313	Approved
0.5923	Remote Similarity	NPD7328	Approved
0.5913	Remote Similarity	NPD5692	Phase 3
0.5909	Remote Similarity	NPD6909	Approved
0.5909	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6908	Approved
0.5902	Remote Similarity	NPD5174	Approved
0.5902	Remote Similarity	NPD5175	Approved
0.5878	Remote Similarity	NPD4522	Approved
0.5878	Remote Similarity	NPD7516	Approved
0.5877	Remote Similarity	NPD6672	Approved
0.5877	Remote Similarity	NPD5737	Approved
0.587	Remote Similarity	NPD7260	Phase 2
0.5868	Remote Similarity	NPD5223	Approved
0.5865	Remote Similarity	NPD8080	Discontinued
0.5862	Remote Similarity	NPD5694	Approved
0.5862	Remote Similarity	NPD5281	Approved
0.5862	Remote Similarity	NPD5284	Approved
0.5862	Remote Similarity	NPD6050	Approved
0.5862	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6695	Phase 3
0.5852	Remote Similarity	NPD8451	Approved
0.5847	Remote Similarity	NPD4629	Approved
0.5847	Remote Similarity	NPD5210	Approved
0.5833	Remote Similarity	NPD8377	Approved
0.5833	Remote Similarity	NPD8294	Approved
0.5827	Remote Similarity	NPD6845	Suspended
0.5821	Remote Similarity	NPD7829	Approved
0.5821	Remote Similarity	NPD7830	Approved
0.5809	Remote Similarity	NPD8448	Approved
0.5806	Remote Similarity	NPD4767	Approved
0.5806	Remote Similarity	NPD4768	Approved
0.5789	Remote Similarity	NPD8380	Approved
0.5789	Remote Similarity	NPD8296	Approved
0.5789	Remote Similarity	NPD8379	Approved
0.5789	Remote Similarity	NPD8378	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