NPASS Compound

Structure

CID58662 OpenBabel06191715392D 26 31 0 0 1 0 0 0 0 0999 V2000 -1.6039 -0.9728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0405 -0.9731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0270 2.7222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1532 2.7217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7810 2.2557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7816 -0.4983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 1.8044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5625 1.8048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5630 0.9020 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5632 3.6088 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5628 1.8042 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3444 3.1576 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7814 0.4511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7818 3.1576 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7813 0.4510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1257 1.8040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7816 2.2553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3445 2.2551 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0001 0.9021 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3846 2.2797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1531 3.6242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0276 2.0456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5627 0.9025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 4.0599 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3442 0.4508 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 6 1 0 0 0 0 2 6 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 20 2 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 9 25 1 6 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 10 24 1 6 0 0 0 11 17 1 6 0 0 0 11 18 1 0 0 0 0 12 18 1 6 0 0 0 12 21 1 0 0 0 0 13 19 1 1 0 0 0 13 23 1 0 0 0 0 14 17 1 6 0 0 0 14 24 1 0 0 0 0 15 19 1 1 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 17 3 1 6 0 0 0 18 4 1 1 0 0 0 19 7 1 1 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.14
Volume:	339.464
LogP:	1.597
LogD:	0.37
LogS:	-4.336
# Rotatable Bonds:	1
TPSA:	97.89
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	6.054
Fsp3:	0.789
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:	-5.385
MDCK Permeability:	6.171849236125126e-05
Pgp-inhibitor:	0.31
Pgp-substrate:	0.912
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.537

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.495
Plasma Protein Binding (PPB):	47.437103271484375%
Volume Distribution (VD):	1.619
Pgp-substrate:	42.8426399230957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.156
CYP3A4-substrate:	0.596

ADMET: Excretion

Clearance (CL):	5.622
Half-life (T1/2):	0.756

ADMET: Toxicity

hERG Blockers:	0.893
Human Hepatotoxicity (H-HT):	0.92
Drug-inuced Liver Injury (DILI):	0.213
AMES Toxicity:	0.189
Rat Oral Acute Toxicity:	0.824
Maximum Recommended Daily Dose:	0.533
Skin Sensitization:	0.594
Carcinogencity:	0.031
Eye Corrosion:	0.065
Eye Irritation:	0.013
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC58662

Natural Product ID:	NPC58662
*Common Name:**	Inumakilactone
IUPAC Name:	n.a.
Synonyms:	Inumakilactone
Standard InCHIKey:	JGSUCIMBMLTPHC-OGSKSCCRSA-N
Standard InCHI:	InChI=1S/C19H22O7/c1-6(2)13-19-7(5-8(20)23-13)17(3)11-9(15(19)26-19)25-16(22)18(11,4)12(21)10-14(17)24-10/h5-6,9-15,21H,1-4H3/t9-,10+,11+,12-,13+,14+,15+,17+,18+,19+/m0/s1
SMILES:	CC(C)[C@@H]1[C@]23C(=CC(=O)O1)[C@]1(C)[C@H]4[C@@H]([C@H]2O3)OC(=O)[C@@]4(C)[C@H]([C@@H]2[C@H]1O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1765575
PubChem CID:	54581281
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO20082	Podocarpus latifolius	Species	Podocarpaceae	Eukaryota	n.a.	root	n.a.	PMID[21306129]
NPO20082	Podocarpus latifolius	Species	Podocarpaceae	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
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	IC50	=	4000.0	nM	PMID[547851]
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	IC50	=	4000.0	nM	PMID[547852]

☑ 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 NPC58662 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	261
0.1-0.2	1527
0.2-0.3	4464
0.3-0.4	7252
0.4-0.5	12980
0.5-0.6	7637
0.6-0.7	6223
0.7-0.8	2085
0.8-0.85	209
0.85-0.9	49
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9533	High Similarity	NPC469655
0.9533	High Similarity	NPC469656
0.9533	High Similarity	NPC474846
0.9279	High Similarity	NPC478204
0.9279	High Similarity	NPC469684
0.9279	High Similarity	NPC53396
0.9279	High Similarity	NPC13713
0.9279	High Similarity	NPC98249
0.9196	High Similarity	NPC284707
0.9196	High Similarity	NPC108581
0.9196	High Similarity	NPC478206
0.9196	High Similarity	NPC478205
0.9159	High Similarity	NPC180744
0.9009	High Similarity	NPC478212
0.8919	High Similarity	NPC269530
0.8919	High Similarity	NPC42658
0.8889	High Similarity	NPC469790
0.887	High Similarity	NPC154491
0.887	High Similarity	NPC251226
0.887	High Similarity	NPC268530
0.8839	High Similarity	NPC475966
0.8818	High Similarity	NPC469370
0.8818	High Similarity	NPC299590
0.8814	High Similarity	NPC293112
0.8803	High Similarity	NPC11895
0.8793	High Similarity	NPC4021
0.8793	High Similarity	NPC159456
0.8783	High Similarity	NPC42673
0.875	High Similarity	NPC222834
0.875	High Similarity	NPC472002
0.8739	High Similarity	NPC253906
0.8739	High Similarity	NPC478209
0.8729	High Similarity	NPC172154
0.8729	High Similarity	NPC81736
0.8718	High Similarity	NPC170538
0.8696	High Similarity	NPC240509
0.8673	High Similarity	NPC477126
0.8661	High Similarity	NPC247031
0.8661	High Similarity	NPC132790
0.8661	High Similarity	NPC100329
0.8661	High Similarity	NPC97939
0.8655	High Similarity	NPC473635
0.8649	High Similarity	NPC478210
0.8644	High Similarity	NPC67251
0.8644	High Similarity	NPC469789
0.8621	High Similarity	NPC230513
0.8596	High Similarity	NPC117712
0.8571	High Similarity	NPC8369
0.8571	High Similarity	NPC24651
0.8571	High Similarity	NPC478211
0.8559	High Similarity	NPC312833
0.8522	High Similarity	NPC207217
0.8509	High Similarity	NPC33360
0.85	High Similarity	NPC120994
0.85	High Similarity	NPC203702
0.85	High Similarity	NPC225049
0.8487	Intermediate Similarity	NPC265557
0.8487	Intermediate Similarity	NPC91693
0.8487	Intermediate Similarity	NPC105926
0.8487	Intermediate Similarity	NPC18945
0.8475	Intermediate Similarity	NPC67569
0.8475	Intermediate Similarity	NPC102822
0.8475	Intermediate Similarity	NPC477046
0.8475	Intermediate Similarity	NPC470779
0.8468	Intermediate Similarity	NPC187435
0.8468	Intermediate Similarity	NPC67321
0.8455	Intermediate Similarity	NPC146731
0.8455	Intermediate Similarity	NPC296950
0.8455	Intermediate Similarity	NPC283850
0.8448	Intermediate Similarity	NPC97908
0.8448	Intermediate Similarity	NPC296822
0.8448	Intermediate Similarity	NPC470775
0.8448	Intermediate Similarity	NPC176513
0.8448	Intermediate Similarity	NPC470854
0.8448	Intermediate Similarity	NPC474654
0.8448	Intermediate Similarity	NPC122033
0.8448	Intermediate Similarity	NPC473590
0.8448	Intermediate Similarity	NPC55296
0.8448	Intermediate Similarity	NPC287343
0.8435	Intermediate Similarity	NPC284915
0.8417	Intermediate Similarity	NPC476729
0.8417	Intermediate Similarity	NPC8374
0.8403	Intermediate Similarity	NPC269642
0.8403	Intermediate Similarity	NPC470265
0.8403	Intermediate Similarity	NPC23786
0.8378	Intermediate Similarity	NPC478208
0.8378	Intermediate Similarity	NPC469607
0.8378	Intermediate Similarity	NPC102352
0.8376	Intermediate Similarity	NPC251310
0.8376	Intermediate Similarity	NPC470776
0.8376	Intermediate Similarity	NPC17772
0.8364	Intermediate Similarity	NPC72842
0.8364	Intermediate Similarity	NPC99510
0.8364	Intermediate Similarity	NPC159533
0.8362	Intermediate Similarity	NPC478216
0.8362	Intermediate Similarity	NPC474333
0.8362	Intermediate Similarity	NPC179626
0.8348	Intermediate Similarity	NPC49451
0.8348	Intermediate Similarity	NPC25909
0.8348	Intermediate Similarity	NPC94509
0.8347	Intermediate Similarity	NPC477745
0.8347	Intermediate Similarity	NPC198209
0.8319	Intermediate Similarity	NPC474243
0.8305	Intermediate Similarity	NPC473636
0.8305	Intermediate Similarity	NPC470777
0.8305	Intermediate Similarity	NPC475041
0.8305	Intermediate Similarity	NPC77689
0.8305	Intermediate Similarity	NPC211093
0.8305	Intermediate Similarity	NPC470186
0.8305	Intermediate Similarity	NPC473839
0.8304	Intermediate Similarity	NPC144854
0.8304	Intermediate Similarity	NPC3316
0.8304	Intermediate Similarity	NPC230541
0.8291	Intermediate Similarity	NPC476712
0.8291	Intermediate Similarity	NPC134430
0.8291	Intermediate Similarity	NPC475809
0.8291	Intermediate Similarity	NPC476713
0.8291	Intermediate Similarity	NPC473968
0.8279	Intermediate Similarity	NPC476008
0.8276	Intermediate Similarity	NPC299849
0.8273	Intermediate Similarity	NPC295791
0.8273	Intermediate Similarity	NPC476081
0.8264	Intermediate Similarity	NPC470922
0.8261	Intermediate Similarity	NPC473877
0.8261	Intermediate Similarity	NPC474516
0.8257	Intermediate Similarity	NPC47024
0.825	Intermediate Similarity	NPC153700
0.825	Intermediate Similarity	NPC88326
0.8246	Intermediate Similarity	NPC5103
0.8246	Intermediate Similarity	NPC235014
0.8246	Intermediate Similarity	NPC472215
0.8246	Intermediate Similarity	NPC472214
0.8235	Intermediate Similarity	NPC475003
0.8235	Intermediate Similarity	NPC112038
0.823	Intermediate Similarity	NPC277017
0.823	Intermediate Similarity	NPC37628
0.823	Intermediate Similarity	NPC306265
0.823	Intermediate Similarity	NPC192813
0.823	Intermediate Similarity	NPC94377
0.823	Intermediate Similarity	NPC275539
0.823	Intermediate Similarity	NPC154608
0.823	Intermediate Similarity	NPC469916
0.823	Intermediate Similarity	NPC472439
0.823	Intermediate Similarity	NPC189075
0.822	Intermediate Similarity	NPC709
0.822	Intermediate Similarity	NPC204552
0.822	Intermediate Similarity	NPC188667
0.822	Intermediate Similarity	NPC50774
0.8214	Intermediate Similarity	NPC470587
0.8205	Intermediate Similarity	NPC474734
0.8205	Intermediate Similarity	NPC96312
0.8205	Intermediate Similarity	NPC328374
0.8205	Intermediate Similarity	NPC476710
0.8205	Intermediate Similarity	NPC89929
0.8205	Intermediate Similarity	NPC213084
0.8205	Intermediate Similarity	NPC190185
0.8205	Intermediate Similarity	NPC270478
0.8205	Intermediate Similarity	NPC251236
0.8205	Intermediate Similarity	NPC476711
0.8205	Intermediate Similarity	NPC471816
0.8205	Intermediate Similarity	NPC40632
0.8198	Intermediate Similarity	NPC61442
0.819	Intermediate Similarity	NPC208998
0.819	Intermediate Similarity	NPC477266
0.819	Intermediate Similarity	NPC7921
0.819	Intermediate Similarity	NPC471204
0.8182	Intermediate Similarity	NPC475958
0.8174	Intermediate Similarity	NPC474229
0.8174	Intermediate Similarity	NPC146945
0.8174	Intermediate Similarity	NPC171888
0.8174	Intermediate Similarity	NPC317107
0.8174	Intermediate Similarity	NPC188738
0.816	Intermediate Similarity	NPC476193
0.8158	Intermediate Similarity	NPC42662
0.8158	Intermediate Similarity	NPC143706
0.8158	Intermediate Similarity	NPC141350
0.8158	Intermediate Similarity	NPC472534
0.8151	Intermediate Similarity	NPC475775
0.8151	Intermediate Similarity	NPC476529
0.8151	Intermediate Similarity	NPC475520
0.8145	Intermediate Similarity	NPC231529
0.8145	Intermediate Similarity	NPC473593
0.8142	Intermediate Similarity	NPC284732
0.8142	Intermediate Similarity	NPC110496
0.8142	Intermediate Similarity	NPC78966
0.8142	Intermediate Similarity	NPC473165
0.8136	Intermediate Similarity	NPC27999
0.8136	Intermediate Similarity	NPC470493
0.8136	Intermediate Similarity	NPC470492
0.8136	Intermediate Similarity	NPC477116
0.8136	Intermediate Similarity	NPC183580
0.8136	Intermediate Similarity	NPC167606
0.8136	Intermediate Similarity	NPC286528
0.8136	Intermediate Similarity	NPC20302
0.8136	Intermediate Similarity	NPC473656
0.8136	Intermediate Similarity	NPC470778
0.8136	Intermediate Similarity	NPC312824
0.8136	Intermediate Similarity	NPC146432
0.8136	Intermediate Similarity	NPC140055
0.813	Intermediate Similarity	NPC42399

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 NPC58662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1764
0.2-0.3	3729
0.3-0.4	2219
0.4-0.5	704
0.5-0.6	294
0.6-0.7	179
0.7-0.8	33
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8818	High Similarity	NPD4061	Clinical (unspecified phase)
0.8571	High Similarity	NPD5955	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD7115	Discovery
0.807	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4225	Approved
0.7717	Intermediate Similarity	NPD7319	Approved
0.7699	Intermediate Similarity	NPD5344	Discontinued
0.7586	Intermediate Similarity	NPD6008	Approved
0.7522	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.748	Intermediate Similarity	NPD7507	Approved
0.7458	Intermediate Similarity	NPD6686	Approved
0.7456	Intermediate Similarity	NPD7639	Approved
0.7456	Intermediate Similarity	NPD7640	Approved
0.7304	Intermediate Similarity	NPD6648	Approved
0.7302	Intermediate Similarity	NPD6921	Approved
0.7302	Intermediate Similarity	NPD8513	Phase 3
0.7295	Intermediate Similarity	NPD4632	Approved
0.7266	Intermediate Similarity	NPD7492	Approved
0.7222	Intermediate Similarity	NPD6054	Approved
0.7222	Intermediate Similarity	NPD6059	Approved
0.7209	Intermediate Similarity	NPD6616	Approved
0.7207	Intermediate Similarity	NPD6698	Approved
0.7207	Intermediate Similarity	NPD46	Approved
0.719	Intermediate Similarity	NPD6371	Approved
0.7188	Intermediate Similarity	NPD8328	Phase 3
0.7165	Intermediate Similarity	NPD6015	Approved
0.7165	Intermediate Similarity	NPD6016	Approved
0.7165	Intermediate Similarity	NPD8515	Approved
0.7165	Intermediate Similarity	NPD8516	Approved
0.7165	Intermediate Similarity	NPD8517	Approved
0.7154	Intermediate Similarity	NPD7078	Approved
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.712	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6370	Approved
0.7109	Intermediate Similarity	NPD5988	Approved
0.7107	Intermediate Similarity	NPD6372	Approved
0.7107	Intermediate Similarity	NPD6373	Approved
0.7099	Intermediate Similarity	NPD7736	Approved
0.7083	Intermediate Similarity	NPD5701	Approved
0.7083	Intermediate Similarity	NPD5697	Approved
0.7073	Intermediate Similarity	NPD6053	Discontinued
0.7073	Intermediate Similarity	NPD8297	Approved
0.7063	Intermediate Similarity	NPD7328	Approved
0.7063	Intermediate Similarity	NPD7327	Approved
0.7049	Intermediate Similarity	NPD4634	Approved
0.7034	Intermediate Similarity	NPD7632	Discontinued
0.7025	Intermediate Similarity	NPD6881	Approved
0.7025	Intermediate Similarity	NPD7320	Approved
0.7025	Intermediate Similarity	NPD6899	Approved
0.6992	Remote Similarity	NPD6650	Approved
0.6992	Remote Similarity	NPD6649	Approved
0.6984	Remote Similarity	NPD6009	Approved
0.6967	Remote Similarity	NPD6012	Approved
0.6967	Remote Similarity	NPD6014	Approved
0.6967	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6013	Approved
0.6957	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7604	Phase 2
0.6911	Remote Similarity	NPD6883	Approved
0.6911	Remote Similarity	NPD7290	Approved
0.6911	Remote Similarity	NPD7102	Approved
0.6899	Remote Similarity	NPD8379	Approved
0.6899	Remote Similarity	NPD8380	Approved
0.6899	Remote Similarity	NPD5983	Phase 2
0.6899	Remote Similarity	NPD8033	Approved
0.6899	Remote Similarity	NPD8335	Approved
0.6899	Remote Similarity	NPD8296	Approved
0.6899	Remote Similarity	NPD8378	Approved
0.6894	Remote Similarity	NPD8074	Phase 3
0.6885	Remote Similarity	NPD6011	Approved
0.6855	Remote Similarity	NPD6869	Approved
0.6855	Remote Similarity	NPD6617	Approved
0.6855	Remote Similarity	NPD8130	Phase 1
0.6855	Remote Similarity	NPD6847	Approved
0.6838	Remote Similarity	NPD4755	Approved
0.6838	Remote Similarity	NPD7902	Approved
0.6822	Remote Similarity	NPD8294	Approved
0.6822	Remote Similarity	NPD8377	Approved
0.6803	Remote Similarity	NPD6412	Phase 2
0.68	Remote Similarity	NPD6882	Approved
0.6783	Remote Similarity	NPD5779	Approved
0.6783	Remote Similarity	NPD6399	Phase 3
0.6783	Remote Similarity	NPD5778	Approved
0.6769	Remote Similarity	NPD7503	Approved
0.6757	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1694	Approved
0.675	Remote Similarity	NPD5211	Phase 2
0.6746	Remote Similarity	NPD8133	Approved
0.6724	Remote Similarity	NPD7748	Approved
0.6723	Remote Similarity	NPD4696	Approved
0.6723	Remote Similarity	NPD5286	Approved
0.6723	Remote Similarity	NPD4700	Approved
0.6723	Remote Similarity	NPD5285	Approved
0.672	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6033	Approved
0.6696	Remote Similarity	NPD6411	Approved
0.6696	Remote Similarity	NPD3618	Phase 1
0.6696	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD7515	Phase 2
0.6692	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6641	Remote Similarity	NPD6274	Approved
0.6639	Remote Similarity	NPD5141	Approved
0.6636	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5224	Approved
0.6612	Remote Similarity	NPD5225	Approved
0.6612	Remote Similarity	NPD5226	Approved
0.6612	Remote Similarity	NPD4633	Approved
0.661	Remote Similarity	NPD4697	Phase 3
0.6609	Remote Similarity	NPD7838	Discovery
0.6581	Remote Similarity	NPD5282	Discontinued
0.6581	Remote Similarity	NPD7900	Approved
0.6581	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5175	Approved
0.6557	Remote Similarity	NPD5174	Approved
0.6555	Remote Similarity	NPD6084	Phase 2
0.6555	Remote Similarity	NPD6083	Phase 2
0.6552	Remote Similarity	NPD7637	Suspended
0.6552	Remote Similarity	NPD6079	Approved
0.6549	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4159	Approved
0.6529	Remote Similarity	NPD5223	Approved
0.6525	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6101	Approved
0.6515	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5696	Approved
0.6496	Remote Similarity	NPD4202	Approved
0.6491	Remote Similarity	NPD3573	Approved
0.6489	Remote Similarity	NPD7101	Approved
0.6489	Remote Similarity	NPD7100	Approved
0.6471	Remote Similarity	NPD5222	Approved
0.6471	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5221	Approved
0.6462	Remote Similarity	NPD6317	Approved
0.6452	Remote Similarity	NPD4767	Approved
0.6452	Remote Similarity	NPD4768	Approved
0.6449	Remote Similarity	NPD7260	Phase 2
0.6441	Remote Similarity	NPD6001	Approved
0.6423	Remote Similarity	NPD4754	Approved
0.6417	Remote Similarity	NPD5173	Approved
0.6412	Remote Similarity	NPD6313	Approved
0.6412	Remote Similarity	NPD6335	Approved
0.6412	Remote Similarity	NPD6314	Approved
0.641	Remote Similarity	NPD8034	Phase 2
0.641	Remote Similarity	NPD8035	Phase 2
0.6403	Remote Similarity	NPD6845	Suspended
0.6391	Remote Similarity	NPD6909	Approved
0.6391	Remote Similarity	NPD6908	Approved
0.6387	Remote Similarity	NPD5695	Phase 3
0.6379	Remote Similarity	NPD1695	Approved
0.6349	Remote Similarity	NPD4730	Approved
0.6349	Remote Similarity	NPD4729	Approved
0.6349	Remote Similarity	NPD5128	Approved
0.6348	Remote Similarity	NPD7524	Approved
0.6339	Remote Similarity	NPD3667	Approved
0.6325	Remote Similarity	NPD5785	Approved
0.6325	Remote Similarity	NPD3168	Discontinued
0.6296	Remote Similarity	NPD6067	Discontinued
0.6296	Remote Similarity	NPD7642	Approved
0.6271	Remote Similarity	NPD5693	Phase 1
0.6261	Remote Similarity	NPD7334	Approved
0.6261	Remote Similarity	NPD7146	Approved
0.6261	Remote Similarity	NPD5330	Approved
0.6261	Remote Similarity	NPD6684	Approved
0.6261	Remote Similarity	NPD6409	Approved
0.6261	Remote Similarity	NPD7521	Approved
0.626	Remote Similarity	NPD6868	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD5251	Approved
0.6239	Remote Similarity	NPD4753	Phase 2
0.623	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4786	Approved
0.6228	Remote Similarity	NPD3666	Approved
0.6228	Remote Similarity	NPD3665	Phase 1
0.6228	Remote Similarity	NPD3133	Approved
0.6224	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD5215	Approved
0.6202	Remote Similarity	NPD5217	Approved
0.6202	Remote Similarity	NPD5216	Approved
0.6176	Remote Similarity	NPD7830	Approved
0.6176	Remote Similarity	NPD7829	Approved
0.6174	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD6672	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