NPASS Compound

Structure

CID235014 OpenBabel06191716032D 23 25 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 15 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 18 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 6 0 0 0 12 15 1 0 0 0 0 12 16 1 6 0 0 0 13 19 2 0 0 0 0 13 23 1 0 0 0 0 14 17 1 1 0 0 0 14 20 1 0 0 0 0 14 23 1 0 0 0 0 16 17 1 1 0 0 0 17 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.16
Volume:	321.751
LogP:	2.657
LogD:	1.327
LogS:	-3.916
# Rotatable Bonds:	2
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	4.834
Fsp3:	0.765
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:	-4.735
MDCK Permeability:	3.124805516563356e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.118
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.444

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.87
Plasma Protein Binding (PPB):	46.320125579833984%
Volume Distribution (VD):	0.758
Pgp-substrate:	71.88385772705078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.549
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.056
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	3.176
Half-life (T1/2):	0.322

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.514
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.971
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.552
Carcinogencity:	0.644
Eye Corrosion:	0.242
Eye Irritation:	0.43
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC235014

Natural Product ID:	NPC235014
*Common Name:**	11-Alpha-Hydroxycinnamosmolide
IUPAC Name:	[(1R,5R,5aS,9aS,9bS)-1,9b-dihydroxy-6,6,9a-trimethyl-3-oxo-1,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-5-yl] acetate
Synonyms:	11-Alpha-Hydroxycinnamosmolide
Standard InCHIKey:	AXYROLCKVUMFEF-ZMNIPVBYSA-N
Standard InCHI:	InChI=1S/C17H24O6/c1-9(18)22-11-8-10-13(19)23-14(20)17(10,21)16(4)7-5-6-15(2,3)12(11)16/h8,11-12,14,20-21H,5-7H2,1-4H3/t11-,12+,14-,16+,17+/m1/s1
SMILES:	CC(=O)O[C@@H]1C=C2C(=O)O[C@H]([C@@]2([C@@]2(C)CCCC(C)(C)[C@H]12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL240943
PubChem CID:	16739250
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO23467	Lobaria scrobiculata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24725159]
NPO4929	Pyropia perforata	Species	Bangiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14437	Rimularia gibbosa	Species	Trapeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23467	Lobaria scrobiculata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22984	Aframomum sceptrum	Species	Zingiberaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5370	Individual Protein	Arylamine N-acetyltransferase	Mycobacterium smegmatis	Inhibition	=	35.0	%	PMID[484885]

☑ 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 NPC235014 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	207
0.1-0.2	1213
0.2-0.3	3984
0.3-0.4	7149
0.4-0.5	12462
0.5-0.6	7779
0.6-0.7	6423
0.7-0.8	3274
0.8-0.85	180
0.85-0.9	23
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9505	High Similarity	NPC146731
0.9505	High Similarity	NPC296950
0.8889	High Similarity	NPC269530
0.8879	High Similarity	NPC5103
0.8846	High Similarity	NPC159533
0.8739	High Similarity	NPC23046
0.8636	High Similarity	NPC469496
0.8636	High Similarity	NPC469463
0.8636	High Similarity	NPC264153
0.8636	High Similarity	NPC469454
0.8624	High Similarity	NPC304180
0.8624	High Similarity	NPC179798
0.8585	High Similarity	NPC258532
0.8571	High Similarity	NPC13713
0.8559	High Similarity	NPC473593
0.8522	High Similarity	NPC287236
0.8496	Intermediate Similarity	NPC475913
0.8468	Intermediate Similarity	NPC56448
0.8447	Intermediate Similarity	NPC240673
0.8447	Intermediate Similarity	NPC17578
0.844	Intermediate Similarity	NPC31522
0.8435	Intermediate Similarity	NPC170084
0.8435	Intermediate Similarity	NPC476204
0.8431	Intermediate Similarity	NPC474555
0.8426	Intermediate Similarity	NPC187435
0.8426	Intermediate Similarity	NPC67321
0.8421	Intermediate Similarity	NPC474179
0.8421	Intermediate Similarity	NPC475834
0.8407	Intermediate Similarity	NPC474483
0.8407	Intermediate Similarity	NPC473968
0.8407	Intermediate Similarity	NPC469684
0.8396	Intermediate Similarity	NPC295791
0.8396	Intermediate Similarity	NPC58329
0.8378	Intermediate Similarity	NPC194951
0.8378	Intermediate Similarity	NPC12046
0.8376	Intermediate Similarity	NPC470922
0.8365	Intermediate Similarity	NPC475709
0.8349	Intermediate Similarity	NPC151393
0.8349	Intermediate Similarity	NPC38948
0.8349	Intermediate Similarity	NPC219900
0.8349	Intermediate Similarity	NPC325054
0.8349	Intermediate Similarity	NPC90946
0.8349	Intermediate Similarity	NPC392
0.8349	Intermediate Similarity	NPC300614
0.8349	Intermediate Similarity	NPC177524
0.8348	Intermediate Similarity	NPC48692
0.8333	Intermediate Similarity	NPC477125
0.8333	Intermediate Similarity	NPC166346
0.8319	Intermediate Similarity	NPC471816
0.8318	Intermediate Similarity	NPC99510
0.8318	Intermediate Similarity	NPC69171
0.8318	Intermediate Similarity	NPC474165
0.8318	Intermediate Similarity	NPC72842
0.8304	Intermediate Similarity	NPC293658
0.8304	Intermediate Similarity	NPC157441
0.8304	Intermediate Similarity	NPC474410
0.8302	Intermediate Similarity	NPC308824
0.8288	Intermediate Similarity	NPC317107
0.8286	Intermediate Similarity	NPC23364
0.8286	Intermediate Similarity	NPC124512
0.8286	Intermediate Similarity	NPC159763
0.8286	Intermediate Similarity	NPC222303
0.8286	Intermediate Similarity	NPC278386
0.8286	Intermediate Similarity	NPC216478
0.8276	Intermediate Similarity	NPC67569
0.8273	Intermediate Similarity	NPC206618
0.8264	Intermediate Similarity	NPC475444
0.8264	Intermediate Similarity	NPC473679
0.8264	Intermediate Similarity	NPC183816
0.8264	Intermediate Similarity	NPC322904
0.8264	Intermediate Similarity	NPC233223
0.8264	Intermediate Similarity	NPC319719
0.8264	Intermediate Similarity	NPC324933
0.8264	Intermediate Similarity	NPC196874
0.8264	Intermediate Similarity	NPC231240
0.8264	Intermediate Similarity	NPC475177
0.8261	Intermediate Similarity	NPC477071
0.8261	Intermediate Similarity	NPC268958
0.8257	Intermediate Similarity	NPC293512
0.8257	Intermediate Similarity	NPC112780
0.8252	Intermediate Similarity	NPC474554
0.825	Intermediate Similarity	NPC476966
0.8246	Intermediate Similarity	NPC58662
0.8246	Intermediate Similarity	NPC475323
0.8246	Intermediate Similarity	NPC98249
0.8246	Intermediate Similarity	NPC473656
0.8246	Intermediate Similarity	NPC53396
0.8235	Intermediate Similarity	NPC42399
0.8224	Intermediate Similarity	NPC472815
0.8224	Intermediate Similarity	NPC223834
0.8224	Intermediate Similarity	NPC183571
0.8214	Intermediate Similarity	NPC321272
0.8214	Intermediate Similarity	NPC317460
0.8214	Intermediate Similarity	NPC317687
0.8214	Intermediate Similarity	NPC328074
0.8214	Intermediate Similarity	NPC470025
0.8214	Intermediate Similarity	NPC472002
0.8214	Intermediate Similarity	NPC236217
0.8208	Intermediate Similarity	NPC47024
0.8205	Intermediate Similarity	NPC23786
0.8205	Intermediate Similarity	NPC470265
0.8198	Intermediate Similarity	NPC46407
0.8198	Intermediate Similarity	NPC474567
0.8198	Intermediate Similarity	NPC119550
0.8197	Intermediate Similarity	NPC316915
0.819	Intermediate Similarity	NPC70145
0.819	Intermediate Similarity	NPC476127
0.819	Intermediate Similarity	NPC91695
0.819	Intermediate Similarity	NPC476150
0.8182	Intermediate Similarity	NPC300655
0.8182	Intermediate Similarity	NPC128795
0.8182	Intermediate Similarity	NPC48548
0.8182	Intermediate Similarity	NPC222951
0.8182	Intermediate Similarity	NPC43589
0.8182	Intermediate Similarity	NPC306265
0.8182	Intermediate Similarity	NPC311178
0.8182	Intermediate Similarity	NPC217921
0.8182	Intermediate Similarity	NPC135015
0.8174	Intermediate Similarity	NPC234522
0.8174	Intermediate Similarity	NPC284707
0.8167	Intermediate Similarity	NPC473620
0.8165	Intermediate Similarity	NPC252296
0.8158	Intermediate Similarity	NPC268954
0.8158	Intermediate Similarity	NPC44170
0.8155	Intermediate Similarity	NPC115021
0.8148	Intermediate Similarity	NPC99266
0.8148	Intermediate Similarity	NPC156681
0.8148	Intermediate Similarity	NPC151516
0.8142	Intermediate Similarity	NPC477126
0.8142	Intermediate Similarity	NPC470027
0.8142	Intermediate Similarity	NPC25909
0.8136	Intermediate Similarity	NPC67251
0.8136	Intermediate Similarity	NPC469789
0.8131	Intermediate Similarity	NPC63249
0.8131	Intermediate Similarity	NPC471075
0.8125	Intermediate Similarity	NPC469655
0.8125	Intermediate Similarity	NPC474846
0.8125	Intermediate Similarity	NPC17791
0.8125	Intermediate Similarity	NPC324683
0.8125	Intermediate Similarity	NPC469656
0.812	Intermediate Similarity	NPC129434
0.812	Intermediate Similarity	NPC46570
0.8113	Intermediate Similarity	NPC187268
0.8113	Intermediate Similarity	NPC316598
0.8108	Intermediate Similarity	NPC40728
0.8108	Intermediate Similarity	NPC474243
0.8108	Intermediate Similarity	NPC316974
0.8108	Intermediate Similarity	NPC143706
0.8108	Intermediate Similarity	NPC42662
0.8108	Intermediate Similarity	NPC472534
0.8103	Intermediate Similarity	NPC122971
0.8103	Intermediate Similarity	NPC476529
0.8103	Intermediate Similarity	NPC475775
0.8103	Intermediate Similarity	NPC473274
0.8091	Intermediate Similarity	NPC184512
0.8091	Intermediate Similarity	NPC88013
0.8091	Intermediate Similarity	NPC125423
0.8091	Intermediate Similarity	NPC143609
0.8087	Intermediate Similarity	NPC477116
0.8087	Intermediate Similarity	NPC27999
0.8083	Intermediate Similarity	NPC470780
0.8083	Intermediate Similarity	NPC298841
0.8073	Intermediate Similarity	NPC474917
0.8073	Intermediate Similarity	NPC283850
0.8073	Intermediate Similarity	NPC220964
0.8073	Intermediate Similarity	NPC475676
0.807	Intermediate Similarity	NPC117712
0.807	Intermediate Similarity	NPC110861
0.807	Intermediate Similarity	NPC181145
0.8067	Intermediate Similarity	NPC24651
0.8067	Intermediate Similarity	NPC8369
0.8067	Intermediate Similarity	NPC318135
0.8058	Intermediate Similarity	NPC165904
0.8058	Intermediate Similarity	NPC65513
0.8058	Intermediate Similarity	NPC179517
0.8056	Intermediate Similarity	NPC469606
0.8056	Intermediate Similarity	NPC134077
0.8056	Intermediate Similarity	NPC471363
0.8056	Intermediate Similarity	NPC238397
0.8056	Intermediate Similarity	NPC164551
0.8056	Intermediate Similarity	NPC273005
0.8056	Intermediate Similarity	NPC137430
0.8056	Intermediate Similarity	NPC476081
0.8056	Intermediate Similarity	NPC31058
0.8053	Intermediate Similarity	NPC126691
0.8053	Intermediate Similarity	NPC42658
0.8053	Intermediate Similarity	NPC222834
0.8053	Intermediate Similarity	NPC476801
0.8051	Intermediate Similarity	NPC107493
0.8051	Intermediate Similarity	NPC473231
0.8049	Intermediate Similarity	NPC478151
0.8037	Intermediate Similarity	NPC473219
0.8037	Intermediate Similarity	NPC476299
0.8037	Intermediate Similarity	NPC474012
0.8037	Intermediate Similarity	NPC470761
0.8036	Intermediate Similarity	NPC472666
0.8036	Intermediate Similarity	NPC83005
0.8036	Intermediate Similarity	NPC161816
0.8036	Intermediate Similarity	NPC478211
0.8036	Intermediate Similarity	NPC115257

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 NPC235014 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1591
0.2-0.3	3578
0.3-0.4	2411
0.4-0.5	815
0.5-0.6	332
0.6-0.7	222
0.7-0.8	27
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8349	Intermediate Similarity	NPD6686	Approved
0.8286	Intermediate Similarity	NPD4225	Approved
0.7931	Intermediate Similarity	NPD7115	Discovery
0.7788	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6371	Approved
0.7667	Intermediate Similarity	NPD8515	Approved
0.7667	Intermediate Similarity	NPD8517	Approved
0.7667	Intermediate Similarity	NPD8516	Approved
0.7667	Intermediate Similarity	NPD8513	Phase 3
0.7661	Intermediate Similarity	NPD7319	Approved
0.7611	Intermediate Similarity	NPD6412	Phase 2
0.7565	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7507	Approved
0.7459	Intermediate Similarity	NPD6370	Approved
0.7456	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7736	Approved
0.7398	Intermediate Similarity	NPD8328	Phase 3
0.7387	Intermediate Similarity	NPD7640	Approved
0.7387	Intermediate Similarity	NPD7639	Approved
0.7377	Intermediate Similarity	NPD7503	Approved
0.736	Intermediate Similarity	NPD8293	Discontinued
0.7339	Intermediate Similarity	NPD7492	Approved
0.7333	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1694	Approved
0.7304	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7638	Approved
0.7295	Intermediate Similarity	NPD6054	Approved
0.7295	Intermediate Similarity	NPD6319	Approved
0.729	Intermediate Similarity	NPD6698	Approved
0.729	Intermediate Similarity	NPD46	Approved
0.728	Intermediate Similarity	NPD6616	Approved
0.7273	Intermediate Similarity	NPD7328	Approved
0.7273	Intermediate Similarity	NPD7327	Approved
0.7241	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD8033	Approved
0.7236	Intermediate Similarity	NPD6016	Approved
0.7236	Intermediate Similarity	NPD6015	Approved
0.7222	Intermediate Similarity	NPD7078	Approved
0.7213	Intermediate Similarity	NPD7516	Approved
0.7203	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD5988	Approved
0.7168	Intermediate Similarity	NPD5344	Discontinued
0.7154	Intermediate Similarity	NPD8294	Approved
0.7154	Intermediate Similarity	NPD6059	Approved
0.7154	Intermediate Similarity	NPD8377	Approved
0.7143	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8380	Approved
0.7097	Intermediate Similarity	NPD8296	Approved
0.7097	Intermediate Similarity	NPD8378	Approved
0.7097	Intermediate Similarity	NPD8379	Approved
0.7097	Intermediate Similarity	NPD8335	Approved
0.7087	Intermediate Similarity	NPD8074	Phase 3
0.7083	Intermediate Similarity	NPD8133	Approved
0.7083	Intermediate Similarity	NPD4632	Approved
0.7049	Intermediate Similarity	NPD6009	Approved
0.7048	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD5778	Approved
0.7	Intermediate Similarity	NPD6053	Discontinued
0.6972	Remote Similarity	NPD5785	Approved
0.6957	Remote Similarity	NPD7632	Discontinued
0.6937	Remote Similarity	NPD5282	Discontinued
0.6923	Remote Similarity	NPD6008	Approved
0.6909	Remote Similarity	NPD7983	Approved
0.6864	Remote Similarity	NPD5697	Approved
0.686	Remote Similarity	NPD8297	Approved
0.686	Remote Similarity	NPD6882	Approved
0.6847	Remote Similarity	NPD6399	Phase 3
0.6833	Remote Similarity	NPD4634	Approved
0.6818	Remote Similarity	NPD7838	Discovery
0.6807	Remote Similarity	NPD6899	Approved
0.6807	Remote Similarity	NPD6881	Approved
0.6783	Remote Similarity	NPD6648	Approved
0.678	Remote Similarity	NPD6402	Approved
0.678	Remote Similarity	NPD5739	Approved
0.678	Remote Similarity	NPD7128	Approved
0.678	Remote Similarity	NPD6675	Approved
0.6777	Remote Similarity	NPD6650	Approved
0.6777	Remote Similarity	NPD6649	Approved
0.6759	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7637	Suspended
0.6754	Remote Similarity	NPD6084	Phase 2
0.6754	Remote Similarity	NPD7902	Approved
0.6754	Remote Similarity	NPD6083	Phase 2
0.675	Remote Similarity	NPD6014	Approved
0.675	Remote Similarity	NPD6373	Approved
0.675	Remote Similarity	NPD6372	Approved
0.675	Remote Similarity	NPD6013	Approved
0.675	Remote Similarity	NPD6012	Approved
0.6726	Remote Similarity	NPD5695	Phase 3
0.6723	Remote Similarity	NPD5701	Approved
0.6719	Remote Similarity	NPD6067	Discontinued
0.6719	Remote Similarity	NPD7642	Approved
0.6696	Remote Similarity	NPD5696	Approved
0.6694	Remote Similarity	NPD6883	Approved
0.6694	Remote Similarity	NPD7290	Approved
0.6694	Remote Similarity	NPD7102	Approved
0.6693	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6033	Approved
0.6639	Remote Similarity	NPD8130	Phase 1
0.6639	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD6847	Approved
0.6637	Remote Similarity	NPD7748	Approved
0.6618	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7260	Phase 2
0.6607	Remote Similarity	NPD6411	Approved
0.6607	Remote Similarity	NPD7515	Phase 2
0.6606	Remote Similarity	NPD3618	Phase 1
0.6589	Remote Similarity	NPD7830	Approved
0.6589	Remote Similarity	NPD7604	Phase 2
0.6589	Remote Similarity	NPD7829	Approved
0.6577	Remote Similarity	NPD1695	Approved
0.6567	Remote Similarity	NPD6845	Suspended
0.6562	Remote Similarity	NPD6921	Approved
0.6555	Remote Similarity	NPD5141	Approved
0.6514	Remote Similarity	NPD5363	Approved
0.6496	Remote Similarity	NPD4696	Approved
0.6496	Remote Similarity	NPD5285	Approved
0.6496	Remote Similarity	NPD5286	Approved
0.6491	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7900	Approved
0.6489	Remote Similarity	NPD8451	Approved
0.6489	Remote Similarity	NPD6336	Discontinued
0.6466	Remote Similarity	NPD4755	Approved
0.646	Remote Similarity	NPD5693	Phase 1
0.646	Remote Similarity	NPD5281	Approved
0.646	Remote Similarity	NPD5284	Approved
0.6455	Remote Similarity	NPD7521	Approved
0.6455	Remote Similarity	NPD5330	Approved
0.6455	Remote Similarity	NPD6684	Approved
0.6455	Remote Similarity	NPD7146	Approved
0.6455	Remote Similarity	NPD7334	Approved
0.6455	Remote Similarity	NPD6409	Approved
0.6439	Remote Similarity	NPD8448	Approved
0.6435	Remote Similarity	NPD5210	Approved
0.6435	Remote Similarity	NPD4629	Approved
0.6435	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4753	Phase 2
0.6429	Remote Similarity	NPD6274	Approved
0.6429	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6101	Approved
0.6422	Remote Similarity	NPD3665	Phase 1
0.6422	Remote Similarity	NPD3666	Approved
0.6422	Remote Similarity	NPD3133	Approved
0.6412	Remote Similarity	NPD8341	Approved
0.6412	Remote Similarity	NPD8299	Approved
0.6412	Remote Similarity	NPD8340	Approved
0.6412	Remote Similarity	NPD8342	Approved
0.6404	Remote Similarity	NPD4202	Approved
0.6396	Remote Similarity	NPD7524	Approved
0.6389	Remote Similarity	NPD3667	Approved
0.6387	Remote Similarity	NPD4633	Approved
0.6387	Remote Similarity	NPD5226	Approved
0.6387	Remote Similarity	NPD5225	Approved
0.6387	Remote Similarity	NPD5224	Approved
0.6379	Remote Similarity	NPD7839	Suspended
0.6371	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4700	Approved
0.6339	Remote Similarity	NPD6903	Approved
0.6339	Remote Similarity	NPD6672	Approved
0.6339	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5737	Approved
0.6333	Remote Similarity	NPD5175	Approved
0.6333	Remote Similarity	NPD5174	Approved
0.6316	Remote Similarity	NPD6079	Approved
0.6308	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4519	Discontinued
0.6306	Remote Similarity	NPD4623	Approved
0.6306	Remote Similarity	NPD4249	Approved
0.6303	Remote Similarity	NPD5223	Approved
0.6296	Remote Similarity	NPD6914	Discontinued
0.6296	Remote Similarity	NPD8391	Approved
0.6296	Remote Similarity	NPD8390	Approved
0.6296	Remote Similarity	NPD8392	Approved
0.6283	Remote Similarity	NPD5328	Approved
0.6279	Remote Similarity	NPD4522	Approved
0.6279	Remote Similarity	NPD7100	Approved
0.6279	Remote Similarity	NPD7101	Approved
0.6273	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4786	Approved
0.626	Remote Similarity	NPD8080	Discontinued
0.625	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD3573	Approved
0.6239	Remote Similarity	NPD4269	Approved
0.6239	Remote Similarity	NPD5222	Approved
0.6239	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4697	Phase 3
0.6239	Remote Similarity	NPD4270	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