NPASS Compound

Structure

NPC270478 OpenBabel07101718242D 27 30 0 0 1 0 0 0 0 0999 V2000 2.1369 4.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 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 5.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 3.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 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 3.8005 3.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3005 4.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 2.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 16 1 0 0 0 0 10 20 1 6 0 0 0 10 27 1 0 0 0 0 11 9 1 1 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 1 0 0 0 13 15 1 0 0 0 0 13 26 1 6 0 0 0 14 18 1 6 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 1 0 0 0 19 24 1 0 0 0 0 20 5 1 1 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	368.6
LogP:	1.326
LogD:	1.097
LogS:	-3.744
# Rotatable Bonds:	3
TPSA:	102.43
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	5.329
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.312
MDCK Permeability:	1.7185466276714578e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.345
30% Bioavailability (F30%):	0.646

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.673
Plasma Protein Binding (PPB):	34.11086654663086%
Volume Distribution (VD):	1.127
Pgp-substrate:	47.791473388671875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.866
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.639
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	5.301
Half-life (T1/2):	0.688

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.511
Drug-inuced Liver Injury (DILI):	0.788
AMES Toxicity:	0.193
Rat Oral Acute Toxicity:	0.897
Maximum Recommended Daily Dose:	0.638
Skin Sensitization:	0.326
Carcinogencity:	0.791
Eye Corrosion:	0.558
Eye Irritation:	0.095
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC270478

Natural Product ID:	NPC270478
*Common Name:**	8Alpha-(2',3'-Epoxy-2'-Methylbutyryloxy)-4Alpha-Hydroxy-9-Oxo-5Betah-Eudesm-1,11(13)-Dien-6Beta,12-Olide
IUPAC Name:	[(3aS,4R,5aS,9R,9aR,9bR)-9-hydroxy-5a,9-dimethyl-3-methylidene-2,5-dioxo-4,8,9a,9b-tetrahydro-3aH-benzo[g][1]benzofuran-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
Synonyms:
Standard InCHIKey:	QYROGYZSVUNCQK-JMTOWNFOSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-9-11-12(25-16(9)22)14-18(3,7-6-8-19(14,4)24)15(21)13(11)26-17(23)20(5)10(2)27-20/h6-7,10-14,24H,1,8H2,2-5H3/t10-,11+,12-,13-,14+,18+,19-,20-/m1/s1
SMILES:	C=C1[C@H]2[C@H]([C@H]3[C@](C)(C=CC[C@@]3(C)O)C(=O)[C@@H]2OC(=O)[C@@]2(C)[C@@H](C)O2)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517638
PubChem CID:	9999579
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
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
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	10.0	uM	PMID[474081]

☑ 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 NPC270478 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	236
0.1-0.2	1347
0.2-0.3	4306
0.3-0.4	7382
0.4-0.5	13096
0.5-0.6	7770
0.6-0.7	6297
0.7-0.8	2018
0.8-0.85	233
0.85-0.9	11
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8929	High Similarity	NPC477509
0.8684	High Similarity	NPC469684
0.8644	High Similarity	NPC24651
0.8584	High Similarity	NPC477126
0.8584	High Similarity	NPC159333
0.8571	High Similarity	NPC317107
0.8547	High Similarity	NPC310511
0.8496	Intermediate Similarity	NPC317687
0.8496	Intermediate Similarity	NPC473877
0.8482	Intermediate Similarity	NPC5103
0.8482	Intermediate Similarity	NPC253906
0.8475	Intermediate Similarity	NPC312833
0.8468	Intermediate Similarity	NPC322903
0.8448	Intermediate Similarity	NPC284707
0.8448	Intermediate Similarity	NPC17772
0.8435	Intermediate Similarity	NPC476710
0.8435	Intermediate Similarity	NPC476711
0.8411	Intermediate Similarity	NPC216478
0.8411	Intermediate Similarity	NPC264378
0.8407	Intermediate Similarity	NPC304180
0.8407	Intermediate Similarity	NPC179798
0.8403	Intermediate Similarity	NPC120724
0.8403	Intermediate Similarity	NPC67251
0.8403	Intermediate Similarity	NPC91693
0.8403	Intermediate Similarity	NPC105926
0.8403	Intermediate Similarity	NPC18945
0.8403	Intermediate Similarity	NPC265557
0.8393	Intermediate Similarity	NPC469370
0.8378	Intermediate Similarity	NPC475587
0.8378	Intermediate Similarity	NPC475510
0.8376	Intermediate Similarity	NPC470777
0.8376	Intermediate Similarity	NPC268958
0.8364	Intermediate Similarity	NPC146731
0.8364	Intermediate Similarity	NPC477127
0.8362	Intermediate Similarity	NPC98249
0.8362	Intermediate Similarity	NPC476712
0.8362	Intermediate Similarity	NPC53396
0.8362	Intermediate Similarity	NPC476713
0.8349	Intermediate Similarity	NPC164551
0.8333	Intermediate Similarity	NPC269530
0.8333	Intermediate Similarity	NPC476729
0.8319	Intermediate Similarity	NPC281624
0.8319	Intermediate Similarity	NPC170538
0.8306	Intermediate Similarity	NPC168879
0.8304	Intermediate Similarity	NPC473595
0.8304	Intermediate Similarity	NPC473939
0.8293	Intermediate Similarity	NPC476852
0.8293	Intermediate Similarity	NPC476862
0.8293	Intermediate Similarity	NPC476863
0.8291	Intermediate Similarity	NPC240509
0.8291	Intermediate Similarity	NPC470776
0.8288	Intermediate Similarity	NPC477125
0.8279	Intermediate Similarity	NPC476859
0.8276	Intermediate Similarity	NPC474333
0.8276	Intermediate Similarity	NPC207217
0.8276	Intermediate Similarity	NPC179626
0.8264	Intermediate Similarity	NPC473635
0.8264	Intermediate Similarity	NPC225049
0.8264	Intermediate Similarity	NPC293112
0.8261	Intermediate Similarity	NPC469463
0.8261	Intermediate Similarity	NPC469496
0.8261	Intermediate Similarity	NPC56448
0.8261	Intermediate Similarity	NPC474271
0.8261	Intermediate Similarity	NPC469454
0.8257	Intermediate Similarity	NPC242666
0.8257	Intermediate Similarity	NPC308824
0.8257	Intermediate Similarity	NPC112613
0.825	Intermediate Similarity	NPC11895
0.825	Intermediate Similarity	NPC469789
0.8246	Intermediate Similarity	NPC474846
0.8246	Intermediate Similarity	NPC469655
0.8246	Intermediate Similarity	NPC469656
0.8235	Intermediate Similarity	NPC470779
0.8235	Intermediate Similarity	NPC67569
0.8235	Intermediate Similarity	NPC102822
0.8235	Intermediate Similarity	NPC477046
0.823	Intermediate Similarity	NPC475922
0.823	Intermediate Similarity	NPC474242
0.823	Intermediate Similarity	NPC42662
0.8226	Intermediate Similarity	NPC33378
0.8226	Intermediate Similarity	NPC254146
0.8226	Intermediate Similarity	NPC6274
0.822	Intermediate Similarity	NPC470186
0.8211	Intermediate Similarity	NPC476851
0.8205	Intermediate Similarity	NPC97908
0.8205	Intermediate Similarity	NPC473590
0.8205	Intermediate Similarity	NPC122033
0.8205	Intermediate Similarity	NPC58662
0.8205	Intermediate Similarity	NPC470854
0.8205	Intermediate Similarity	NPC474654
0.8205	Intermediate Similarity	NPC296822
0.8205	Intermediate Similarity	NPC287343
0.8198	Intermediate Similarity	NPC296950
0.8198	Intermediate Similarity	NPC283850
0.8198	Intermediate Similarity	NPC258532
0.819	Intermediate Similarity	NPC238667
0.819	Intermediate Similarity	NPC299849
0.819	Intermediate Similarity	NPC473798
0.8182	Intermediate Similarity	NPC470922
0.8182	Intermediate Similarity	NPC172154
0.8182	Intermediate Similarity	NPC8369
0.8182	Intermediate Similarity	NPC81736
0.8174	Intermediate Similarity	NPC265391
0.8167	Intermediate Similarity	NPC23786
0.8167	Intermediate Similarity	NPC470265
0.8158	Intermediate Similarity	NPC473843
0.8158	Intermediate Similarity	NPC473594
0.8158	Intermediate Similarity	NPC474586
0.8158	Intermediate Similarity	NPC473975
0.8158	Intermediate Similarity	NPC474567
0.8158	Intermediate Similarity	NPC161816
0.8158	Intermediate Similarity	NPC115257
0.8145	Intermediate Similarity	NPC476855
0.8142	Intermediate Similarity	NPC94377
0.8125	Intermediate Similarity	NPC475802
0.8125	Intermediate Similarity	NPC9303
0.8125	Intermediate Similarity	NPC16313
0.812	Intermediate Similarity	NPC96312
0.812	Intermediate Similarity	NPC213084
0.812	Intermediate Similarity	NPC251236
0.812	Intermediate Similarity	NPC190185
0.812	Intermediate Similarity	NPC40632
0.812	Intermediate Similarity	NPC328374
0.8115	Intermediate Similarity	NPC181999
0.8108	Intermediate Similarity	NPC99510
0.8108	Intermediate Similarity	NPC474166
0.8108	Intermediate Similarity	NPC19239
0.8108	Intermediate Similarity	NPC156681
0.8103	Intermediate Similarity	NPC49451
0.8103	Intermediate Similarity	NPC33360
0.8099	Intermediate Similarity	NPC472399
0.8099	Intermediate Similarity	NPC473802
0.8091	Intermediate Similarity	NPC476270
0.8091	Intermediate Similarity	NPC475958
0.8091	Intermediate Similarity	NPC207885
0.8091	Intermediate Similarity	NPC111292
0.8087	Intermediate Similarity	NPC194619
0.8087	Intermediate Similarity	NPC474229
0.808	Intermediate Similarity	NPC102316
0.807	Intermediate Similarity	NPC87335
0.8067	Intermediate Similarity	NPC472933
0.8067	Intermediate Similarity	NPC476960
0.8067	Intermediate Similarity	NPC475520
0.8067	Intermediate Similarity	NPC469488
0.8065	Intermediate Similarity	NPC264192
0.8065	Intermediate Similarity	NPC476854
0.8056	Intermediate Similarity	NPC94337
0.8056	Intermediate Similarity	NPC228766
0.8056	Intermediate Similarity	NPC473964
0.8056	Intermediate Similarity	NPC165528
0.8056	Intermediate Similarity	NPC284518
0.8053	Intermediate Similarity	NPC324327
0.8053	Intermediate Similarity	NPC474421
0.8053	Intermediate Similarity	NPC266514
0.8053	Intermediate Similarity	NPC72813
0.8053	Intermediate Similarity	NPC144854
0.8053	Intermediate Similarity	NPC474716
0.8053	Intermediate Similarity	NPC3316
0.8053	Intermediate Similarity	NPC326994
0.8053	Intermediate Similarity	NPC194620
0.8053	Intermediate Similarity	NPC180744
0.8051	Intermediate Similarity	NPC176513
0.8051	Intermediate Similarity	NPC27999
0.8051	Intermediate Similarity	NPC470775
0.8051	Intermediate Similarity	NPC477116
0.8051	Intermediate Similarity	NPC23046
0.8051	Intermediate Similarity	NPC474518
0.8049	Intermediate Similarity	NPC476008
0.8049	Intermediate Similarity	NPC287423
0.8037	Intermediate Similarity	NPC471446
0.8037	Intermediate Similarity	NPC474841
0.8037	Intermediate Similarity	NPC473434
0.8036	Intermediate Similarity	NPC472756
0.8036	Intermediate Similarity	NPC474741
0.8034	Intermediate Similarity	NPC323821
0.8034	Intermediate Similarity	NPC117712
0.8034	Intermediate Similarity	NPC143268
0.8034	Intermediate Similarity	NPC45218
0.8034	Intermediate Similarity	NPC73314
0.8034	Intermediate Similarity	NPC268238
0.8033	Intermediate Similarity	NPC473919
0.8033	Intermediate Similarity	NPC473709
0.8018	Intermediate Similarity	NPC478176
0.8018	Intermediate Similarity	NPC39996
0.8017	Intermediate Similarity	NPC474516
0.8017	Intermediate Similarity	NPC162009
0.8017	Intermediate Similarity	NPC257017
0.8	Intermediate Similarity	NPC469551
0.8	Intermediate Similarity	NPC472215
0.8	Intermediate Similarity	NPC471126
0.8	Intermediate Similarity	NPC107338
0.8	Intermediate Similarity	NPC471128
0.8	Intermediate Similarity	NPC472214
0.8	Intermediate Similarity	NPC145182
0.8	Intermediate Similarity	NPC89408
0.8	Intermediate Similarity	NPC235014
0.8	Intermediate Similarity	NPC157252
0.8	Intermediate Similarity	NPC47024
0.8	Intermediate Similarity	NPC112038
0.8	Intermediate Similarity	NPC109607

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 NPC270478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1657
0.2-0.3	3696
0.3-0.4	2320
0.4-0.5	771
0.5-0.6	271
0.6-0.7	173
0.7-0.8	61
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7899	Intermediate Similarity	NPD7115	Discovery
0.7851	Intermediate Similarity	NPD6319	Approved
0.7826	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7492	Approved
0.7705	Intermediate Similarity	NPD6054	Approved
0.7692	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6616	Approved
0.7642	Intermediate Similarity	NPD6016	Approved
0.7642	Intermediate Similarity	NPD6015	Approved
0.7619	Intermediate Similarity	NPD7078	Approved
0.7607	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4225	Approved
0.7586	Intermediate Similarity	NPD5697	Approved
0.7581	Intermediate Similarity	NPD5988	Approved
0.7581	Intermediate Similarity	NPD6370	Approved
0.7563	Intermediate Similarity	NPD8297	Approved
0.7559	Intermediate Similarity	NPD7736	Approved
0.7521	Intermediate Similarity	NPD6881	Approved
0.7521	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.7479	Intermediate Similarity	NPD6650	Approved
0.7479	Intermediate Similarity	NPD6649	Approved
0.7459	Intermediate Similarity	NPD6009	Approved
0.7458	Intermediate Similarity	NPD6013	Approved
0.7458	Intermediate Similarity	NPD6014	Approved
0.7458	Intermediate Similarity	NPD6012	Approved
0.7436	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6059	Approved
0.7395	Intermediate Similarity	NPD6883	Approved
0.7395	Intermediate Similarity	NPD7102	Approved
0.7395	Intermediate Similarity	NPD7290	Approved
0.7381	Intermediate Similarity	NPD7604	Phase 2
0.7373	Intermediate Similarity	NPD6011	Approved
0.736	Intermediate Similarity	NPD5983	Phase 2
0.735	Intermediate Similarity	NPD7128	Approved
0.735	Intermediate Similarity	NPD6675	Approved
0.735	Intermediate Similarity	NPD5739	Approved
0.735	Intermediate Similarity	NPD6402	Approved
0.7344	Intermediate Similarity	NPD8293	Discontinued
0.7333	Intermediate Similarity	NPD6617	Approved
0.7333	Intermediate Similarity	NPD6869	Approved
0.7333	Intermediate Similarity	NPD6847	Approved
0.7333	Intermediate Similarity	NPD8130	Phase 1
0.7311	Intermediate Similarity	NPD6373	Approved
0.7311	Intermediate Similarity	NPD6372	Approved
0.7288	Intermediate Similarity	NPD5701	Approved
0.7281	Intermediate Similarity	NPD5696	Approved
0.7273	Intermediate Similarity	NPD6882	Approved
0.725	Intermediate Similarity	NPD4634	Approved
0.7244	Intermediate Similarity	NPD8328	Phase 3
0.7232	Intermediate Similarity	NPD5282	Discontinued
0.7227	Intermediate Similarity	NPD7320	Approved
0.7168	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6336	Discontinued
0.713	Intermediate Similarity	NPD1694	Approved
0.7121	Intermediate Similarity	NPD7260	Phase 2
0.7107	Intermediate Similarity	NPD6371	Approved
0.7094	Intermediate Similarity	NPD5211	Phase 2
0.7087	Intermediate Similarity	NPD6921	Approved
0.7069	Intermediate Similarity	NPD5286	Approved
0.7069	Intermediate Similarity	NPD4696	Approved
0.7069	Intermediate Similarity	NPD6648	Approved
0.7069	Intermediate Similarity	NPD5285	Approved
0.704	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5695	Phase 3
0.6991	Remote Similarity	NPD6399	Phase 3
0.6983	Remote Similarity	NPD7638	Approved
0.6975	Remote Similarity	NPD5141	Approved
0.6972	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7319	Approved
0.696	Remote Similarity	NPD6274	Approved
0.6953	Remote Similarity	NPD8516	Approved
0.6953	Remote Similarity	NPD8513	Phase 3
0.6953	Remote Similarity	NPD8517	Approved
0.6953	Remote Similarity	NPD8515	Approved
0.6949	Remote Similarity	NPD5225	Approved
0.6949	Remote Similarity	NPD5224	Approved
0.6949	Remote Similarity	NPD5226	Approved
0.6949	Remote Similarity	NPD4633	Approved
0.6942	Remote Similarity	NPD6686	Approved
0.6929	Remote Similarity	NPD7101	Approved
0.6929	Remote Similarity	NPD7100	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD7640	Approved
0.6911	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6317	Approved
0.6897	Remote Similarity	NPD4755	Approved
0.6897	Remote Similarity	NPD6084	Phase 2
0.6897	Remote Similarity	NPD6083	Phase 2
0.6897	Remote Similarity	NPD7902	Approved
0.6894	Remote Similarity	NPD6033	Approved
0.6891	Remote Similarity	NPD5174	Approved
0.6891	Remote Similarity	NPD5175	Approved
0.687	Remote Similarity	NPD5210	Approved
0.687	Remote Similarity	NPD4629	Approved
0.6864	Remote Similarity	NPD5223	Approved
0.6864	Remote Similarity	NPD1700	Approved
0.685	Remote Similarity	NPD6314	Approved
0.685	Remote Similarity	NPD6313	Approved
0.685	Remote Similarity	NPD6335	Approved
0.6842	Remote Similarity	NPD5779	Approved
0.6842	Remote Similarity	NPD5778	Approved
0.6822	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6845	Suspended
0.6814	Remote Similarity	NPD46	Approved
0.6814	Remote Similarity	NPD6698	Approved
0.681	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5222	Approved
0.681	Remote Similarity	NPD5221	Approved
0.6783	Remote Similarity	NPD7748	Approved
0.678	Remote Similarity	NPD4700	Approved
0.6754	Remote Similarity	NPD6411	Approved
0.6754	Remote Similarity	NPD5693	Phase 1
0.6752	Remote Similarity	NPD5173	Approved
0.6742	Remote Similarity	NPD7507	Approved
0.6726	Remote Similarity	NPD1695	Approved
0.6696	Remote Similarity	NPD3573	Approved
0.6693	Remote Similarity	NPD6868	Approved
0.6692	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.664	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7900	Approved
0.6637	Remote Similarity	NPD5737	Approved
0.6637	Remote Similarity	NPD6672	Approved
0.6613	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7515	Phase 2
0.6609	Remote Similarity	NPD6079	Approved
0.6607	Remote Similarity	NPD3618	Phase 1
0.6607	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6053	Discontinued
0.6585	Remote Similarity	NPD6412	Phase 2
0.6581	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6101	Approved
0.6565	Remote Similarity	NPD6908	Approved
0.6565	Remote Similarity	NPD6909	Approved
0.656	Remote Similarity	NPD5247	Approved
0.656	Remote Similarity	NPD5248	Approved
0.656	Remote Similarity	NPD5249	Phase 3
0.656	Remote Similarity	NPD5250	Approved
0.656	Remote Similarity	NPD5251	Approved
0.6545	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5128	Approved
0.6522	Remote Similarity	NPD7838	Discovery
0.6522	Remote Similarity	NPD5785	Approved
0.6508	Remote Similarity	NPD5217	Approved
0.6508	Remote Similarity	NPD5216	Approved
0.6508	Remote Similarity	NPD5215	Approved
0.6504	Remote Similarity	NPD4767	Approved
0.6504	Remote Similarity	NPD4768	Approved
0.65	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4754	Approved
0.6466	Remote Similarity	NPD5694	Approved
0.6466	Remote Similarity	NPD7983	Approved
0.6466	Remote Similarity	NPD5281	Approved
0.6466	Remote Similarity	NPD5284	Approved
0.6466	Remote Similarity	NPD7637	Suspended
0.6462	Remote Similarity	NPD7327	Approved
0.6462	Remote Similarity	NPD7328	Approved
0.6454	Remote Similarity	NPD6334	Approved
0.6454	Remote Similarity	NPD6333	Approved
0.6439	Remote Similarity	NPD7503	Approved
0.6435	Remote Similarity	NPD6904	Approved
0.6435	Remote Similarity	NPD6080	Approved
0.6435	Remote Similarity	NPD4753	Phase 2
0.6435	Remote Similarity	NPD6673	Approved
0.6435	Remote Similarity	NPD5328	Approved
0.6429	Remote Similarity	NPD5135	Approved
0.6429	Remote Similarity	NPD5169	Approved
0.6429	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD7516	Approved
0.641	Remote Similarity	NPD4202	Approved
0.6406	Remote Similarity	NPD8133	Approved
0.6396	Remote Similarity	NPD3667	Approved
0.6393	Remote Similarity	NPD7632	Discontinued
0.6379	Remote Similarity	NPD5692	Phase 3
0.6378	Remote Similarity	NPD5127	Approved
0.6364	Remote Similarity	NPD4695	Discontinued
0.6356	Remote Similarity	NPD6001	Approved
0.6325	Remote Similarity	NPD6050	Approved
0.6325	Remote Similarity	NPD8035	Phase 2
0.6325	Remote Similarity	NPD8034	Phase 2
0.632	Remote Similarity	NPD6614	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD8335	Approved
0.6316	Remote Similarity	NPD8379	Approved
0.6316	Remote Similarity	NPD8380	Approved
0.6316	Remote Similarity	NPD6098	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD5690	Phase 2
0.6316	Remote Similarity	NPD7521	Approved
0.6316	Remote Similarity	NPD8296	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