NPASS Compound

Structure

NPC146731 OpenBabel07101719242D 22 24 0 0 1 0 0 0 0 0999 V2000 1.6628 -2.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9742 -0.3514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4542 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9130 0.2967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 -2.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -0.9600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6628 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9130 -1.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 0.4800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3255 -2.8800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2097 -2.1697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3905 0.8770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4773 -0.4800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 -1.4400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 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 11 2 0 0 0 0 8 12 1 0 0 0 0 9 17 1 0 0 0 0 9 21 1 0 0 0 0 10 18 2 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 6 0 0 0 13 15 1 0 0 0 0 13 16 1 6 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 16 17 1 1 0 0 0 17 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.16
Volume:	312.961
LogP:	2.959
LogD:	2.257
LogS:	-4.022
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.752
Synthetic Accessibility Score:	4.693
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:	-4.783
MDCK Permeability:	3.2769192330306396e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.943
Plasma Protein Binding (PPB):	52.787200927734375%
Volume Distribution (VD):	0.796
Pgp-substrate:	72.22247314453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.566
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.27
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	5.262
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.614
Carcinogencity:	0.689
Eye Corrosion:	0.376
Eye Irritation:	0.323
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC146731

Natural Product ID:	NPC146731
*Common Name:**	Cinnamosmolide
IUPAC Name:	[(5R,5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-3-oxo-1,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-5-yl] acetate
Synonyms:	NSC-277292
Standard InCHIKey:	PSJFPRLDKNCZGQ-OSRSDYAFSA-N
Standard InCHI:	InChI=1S/C17H24O5/c1-10(18)22-12-8-11-14(19)21-9-17(11,20)16(4)7-5-6-15(2,3)13(12)16/h8,12-13,20H,5-7,9H2,1-4H3/t12-,13+,16+,17-/m1/s1
SMILES:	CC(=O)O[C@@H]1C=C2C(=O)OC[C@@]2([C@@]2([C@@H]1C(C)(C)CCC2)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402739
PubChem CID:	12303262
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
NPO7432	Pleodendron costaricense	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872133]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18179176]
NPO33473	capsicodendron dinisii	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7400822]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7432	Pleodendron costaricense	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
IC50	1
MIC	8
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	8
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1300.0	nM	PMID[545747]
NPT2	Others	Unspecified		Inhibition	=	20.0	%	PMID[545744]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.2	ug ml-1	PMID[545745]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	125.0	ug.mL-1	PMID[545746]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	156.0	ug.mL-1	PMID[545746]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	23.4	ug.mL-1	PMID[545746]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	625.0	ug.mL-1	PMID[545746]
NPT4952	Organism	Candida shehatae	Candida shehatae	MIC	=	625.0	ug.mL-1	PMID[545746]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	1250.0	ug.mL-1	PMID[545746]
NPT3686	Organism	Exophiala dermatitidis	Exophiala dermatitidis	MIC	=	313.0	ug.mL-1	PMID[545746]
NPT3617	Organism	Pseudallescheria boydii	Pseudallescheria boydii	MIC	=	78.1	ug.mL-1	PMID[545746]

☑ 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 NPC146731 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	196
0.1-0.2	1133
0.2-0.3	3786
0.3-0.4	6927
0.4-0.5	13119
0.5-0.6	7421
0.6-0.7	6476
0.7-0.8	3450
0.8-0.85	158
0.85-0.9	23
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC296950
0.9505	High Similarity	NPC235014
0.932	High Similarity	NPC269530
0.9126	High Similarity	NPC5103
0.91	High Similarity	NPC159533
0.9038	High Similarity	NPC179798
0.9038	High Similarity	NPC304180
0.8868	High Similarity	NPC469496
0.8868	High Similarity	NPC469454
0.8868	High Similarity	NPC469463
0.8868	High Similarity	NPC56448
0.8824	High Similarity	NPC258532
0.8738	High Similarity	NPC477125
0.8725	High Similarity	NPC99510
0.8654	High Similarity	NPC187435
0.8654	High Similarity	NPC67321
0.8627	High Similarity	NPC183571
0.8627	High Similarity	NPC295791
0.8624	High Similarity	NPC469684
0.8624	High Similarity	NPC23046
0.8571	High Similarity	NPC151393
0.8544	High Similarity	NPC72842
0.8544	High Similarity	NPC474165
0.8544	High Similarity	NPC69171
0.8529	High Similarity	NPC308824
0.8519	High Similarity	NPC477126
0.8515	High Similarity	NPC222303
0.8515	High Similarity	NPC23364
0.8515	High Similarity	NPC159763
0.8515	High Similarity	NPC124512
0.8515	High Similarity	NPC216478
0.8515	High Similarity	NPC278386
0.8505	High Similarity	NPC317107
0.8482	Intermediate Similarity	NPC67569
0.8476	Intermediate Similarity	NPC112780
0.8462	Intermediate Similarity	NPC283850
0.8455	Intermediate Similarity	NPC473656
0.8455	Intermediate Similarity	NPC475323
0.8455	Intermediate Similarity	NPC58662
0.8455	Intermediate Similarity	NPC53396
0.8455	Intermediate Similarity	NPC98249
0.8447	Intermediate Similarity	NPC58329
0.8431	Intermediate Similarity	NPC47024
0.8426	Intermediate Similarity	NPC236217
0.8426	Intermediate Similarity	NPC472002
0.8426	Intermediate Similarity	NPC317687
0.8416	Intermediate Similarity	NPC70145
0.8416	Intermediate Similarity	NPC91695
0.8407	Intermediate Similarity	NPC470265
0.8407	Intermediate Similarity	NPC23786
0.8396	Intermediate Similarity	NPC306265
0.8396	Intermediate Similarity	NPC94377
0.8384	Intermediate Similarity	NPC115021
0.8384	Intermediate Similarity	NPC475657
0.8378	Intermediate Similarity	NPC284707
0.8378	Intermediate Similarity	NPC475372
0.8367	Intermediate Similarity	NPC15059
0.8365	Intermediate Similarity	NPC99266
0.8365	Intermediate Similarity	NPC156681
0.8364	Intermediate Similarity	NPC270478
0.8349	Intermediate Similarity	NPC25909
0.8333	Intermediate Similarity	NPC469656
0.8333	Intermediate Similarity	NPC67251
0.8333	Intermediate Similarity	NPC316598
0.8333	Intermediate Similarity	NPC324683
0.8333	Intermediate Similarity	NPC469789
0.8333	Intermediate Similarity	NPC469655
0.8333	Intermediate Similarity	NPC474846
0.8319	Intermediate Similarity	NPC46570
0.8318	Intermediate Similarity	NPC474243
0.8318	Intermediate Similarity	NPC42662
0.8304	Intermediate Similarity	NPC312536
0.8302	Intermediate Similarity	NPC143609
0.8288	Intermediate Similarity	NPC473968
0.8286	Intermediate Similarity	NPC475676
0.8286	Intermediate Similarity	NPC220964
0.8283	Intermediate Similarity	NPC303697
0.8283	Intermediate Similarity	NPC252433
0.8276	Intermediate Similarity	NPC204556
0.8273	Intermediate Similarity	NPC117712
0.8269	Intermediate Similarity	NPC469606
0.8269	Intermediate Similarity	NPC164551
0.8269	Intermediate Similarity	NPC472552
0.8269	Intermediate Similarity	NPC476081
0.8269	Intermediate Similarity	NPC273005
0.8269	Intermediate Similarity	NPC31058
0.8269	Intermediate Similarity	NPC137430
0.8261	Intermediate Similarity	NPC8369
0.8261	Intermediate Similarity	NPC470922
0.8261	Intermediate Similarity	NPC24651
0.8257	Intermediate Similarity	NPC42658
0.8257	Intermediate Similarity	NPC126691
0.8257	Intermediate Similarity	NPC476801
0.8252	Intermediate Similarity	NPC474012
0.8252	Intermediate Similarity	NPC476299
0.8252	Intermediate Similarity	NPC54705
0.8246	Intermediate Similarity	NPC107493
0.8241	Intermediate Similarity	NPC474567
0.8241	Intermediate Similarity	NPC161816
0.8241	Intermediate Similarity	NPC478211
0.8241	Intermediate Similarity	NPC29133
0.8241	Intermediate Similarity	NPC115257
0.8241	Intermediate Similarity	NPC253906
0.8235	Intermediate Similarity	NPC474395
0.8235	Intermediate Similarity	NPC73911
0.8224	Intermediate Similarity	NPC37628
0.8224	Intermediate Similarity	NPC469916
0.8224	Intermediate Similarity	NPC275539
0.8224	Intermediate Similarity	NPC189075
0.8224	Intermediate Similarity	NPC322903
0.8224	Intermediate Similarity	NPC472439
0.8218	Intermediate Similarity	NPC183012
0.8214	Intermediate Similarity	NPC108581
0.8214	Intermediate Similarity	NPC186525
0.8214	Intermediate Similarity	NPC50774
0.8214	Intermediate Similarity	NPC478206
0.8214	Intermediate Similarity	NPC709
0.8214	Intermediate Similarity	NPC478205
0.8208	Intermediate Similarity	NPC1679
0.8208	Intermediate Similarity	NPC469607
0.8208	Intermediate Similarity	NPC111952
0.82	Intermediate Similarity	NPC475912
0.8198	Intermediate Similarity	NPC64318
0.8198	Intermediate Similarity	NPC176840
0.819	Intermediate Similarity	NPC293112
0.819	Intermediate Similarity	NPC4620
0.819	Intermediate Similarity	NPC8196
0.819	Intermediate Similarity	NPC61442
0.8182	Intermediate Similarity	NPC471204
0.8182	Intermediate Similarity	NPC264153
0.8182	Intermediate Similarity	NPC478212
0.8182	Intermediate Similarity	NPC473535
0.8182	Intermediate Similarity	NPC472307
0.8173	Intermediate Similarity	NPC244456
0.8173	Intermediate Similarity	NPC242666
0.8173	Intermediate Similarity	NPC97435
0.8173	Intermediate Similarity	NPC472554
0.8173	Intermediate Similarity	NPC469657
0.8165	Intermediate Similarity	NPC470961
0.8165	Intermediate Similarity	NPC247031
0.8165	Intermediate Similarity	NPC188738
0.8165	Intermediate Similarity	NPC97939
0.8165	Intermediate Similarity	NPC132790
0.8165	Intermediate Similarity	NPC100329
0.8148	Intermediate Similarity	NPC475922
0.8148	Intermediate Similarity	NPC469370
0.8142	Intermediate Similarity	NPC77689
0.8142	Intermediate Similarity	NPC473636
0.8142	Intermediate Similarity	NPC268958
0.8137	Intermediate Similarity	NPC134072
0.8137	Intermediate Similarity	NPC234993
0.8137	Intermediate Similarity	NPC473964
0.8137	Intermediate Similarity	NPC284518
0.8137	Intermediate Similarity	NPC202833
0.8137	Intermediate Similarity	NPC242848
0.8136	Intermediate Similarity	NPC473593
0.8131	Intermediate Similarity	NPC284732
0.8131	Intermediate Similarity	NPC180744
0.8131	Intermediate Similarity	NPC78966
0.8131	Intermediate Similarity	NPC230541
0.8131	Intermediate Similarity	NPC110496
0.8125	Intermediate Similarity	NPC286528
0.8125	Intermediate Similarity	NPC20302
0.8125	Intermediate Similarity	NPC312824
0.8125	Intermediate Similarity	NPC478204
0.8125	Intermediate Similarity	NPC140055
0.8125	Intermediate Similarity	NPC470492
0.8125	Intermediate Similarity	NPC470493
0.8125	Intermediate Similarity	NPC13713
0.8125	Intermediate Similarity	NPC176513
0.8125	Intermediate Similarity	NPC470775
0.8125	Intermediate Similarity	NPC167606
0.8125	Intermediate Similarity	NPC183580
0.8125	Intermediate Similarity	NPC134430
0.8119	Intermediate Similarity	NPC477129
0.8119	Intermediate Similarity	NPC57117
0.8119	Intermediate Similarity	NPC477130
0.8119	Intermediate Similarity	NPC470697
0.8113	Intermediate Similarity	NPC203659
0.8108	Intermediate Similarity	NPC474181
0.8108	Intermediate Similarity	NPC147912
0.8108	Intermediate Similarity	NPC67259
0.8103	Intermediate Similarity	NPC172154
0.8103	Intermediate Similarity	NPC476729
0.8103	Intermediate Similarity	NPC81736
0.8103	Intermediate Similarity	NPC8374
0.81	Intermediate Similarity	NPC186363
0.81	Intermediate Similarity	NPC233345
0.81	Intermediate Similarity	NPC472814
0.81	Intermediate Similarity	NPC177037
0.8095	Intermediate Similarity	NPC162973
0.8095	Intermediate Similarity	NPC165250
0.8091	Intermediate Similarity	NPC265391
0.8091	Intermediate Similarity	NPC470063
0.8091	Intermediate Similarity	NPC277769
0.8091	Intermediate Similarity	NPC191620
0.8091	Intermediate Similarity	NPC90952
0.8091	Intermediate Similarity	NPC473877
0.8087	Intermediate Similarity	NPC170538
0.8087	Intermediate Similarity	NPC312833

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 NPC146731 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1457
0.2-0.3	3529
0.3-0.4	2504
0.4-0.5	896
0.5-0.6	328
0.6-0.7	246
0.7-0.8	28
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
0.8515	High Similarity	NPD4225	Approved
0.8125	Intermediate Similarity	NPD7115	Discovery
0.7982	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD6371	Approved
0.789	Intermediate Similarity	NPD6686	Approved
0.7798	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1694	Approved
0.7636	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD7639	Approved
0.757	Intermediate Similarity	NPD7640	Approved
0.7477	Intermediate Similarity	NPD7638	Approved
0.7476	Intermediate Similarity	NPD46	Approved
0.7476	Intermediate Similarity	NPD6698	Approved
0.7458	Intermediate Similarity	NPD6319	Approved
0.7411	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD5344	Discontinued
0.7264	Intermediate Similarity	NPD5282	Discontinued
0.7258	Intermediate Similarity	NPD7319	Approved
0.725	Intermediate Similarity	NPD8517	Approved
0.725	Intermediate Similarity	NPD8516	Approved
0.725	Intermediate Similarity	NPD8513	Phase 3
0.725	Intermediate Similarity	NPD8515	Approved
0.7241	Intermediate Similarity	NPD4632	Approved
0.7232	Intermediate Similarity	NPD6008	Approved
0.7213	Intermediate Similarity	NPD7492	Approved
0.717	Intermediate Similarity	NPD5779	Approved
0.717	Intermediate Similarity	NPD6399	Phase 3
0.717	Intermediate Similarity	NPD5778	Approved
0.7168	Intermediate Similarity	NPD6412	Phase 2
0.7167	Intermediate Similarity	NPD6054	Approved
0.7155	Intermediate Similarity	NPD6053	Discontinued
0.7154	Intermediate Similarity	NPD7507	Approved
0.7154	Intermediate Similarity	NPD6616	Approved
0.7143	Intermediate Similarity	NPD5785	Approved
0.7117	Intermediate Similarity	NPD7632	Discontinued
0.7107	Intermediate Similarity	NPD6016	Approved
0.7107	Intermediate Similarity	NPD6015	Approved
0.7097	Intermediate Similarity	NPD7078	Approved
0.7091	Intermediate Similarity	NPD6648	Approved
0.7087	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7983	Approved
0.7069	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7902	Approved
0.7049	Intermediate Similarity	NPD5988	Approved
0.7049	Intermediate Similarity	NPD6370	Approved
0.704	Intermediate Similarity	NPD7736	Approved
0.7037	Intermediate Similarity	NPD5695	Phase 3
0.7025	Intermediate Similarity	NPD6059	Approved
0.7018	Intermediate Similarity	NPD5697	Approved
0.7009	Intermediate Similarity	NPD8297	Approved
0.7	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD8328	Phase 3
0.699	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4634	Approved
0.6981	Remote Similarity	NPD7838	Discovery
0.6967	Remote Similarity	NPD7503	Approved
0.696	Remote Similarity	NPD8293	Discontinued
0.696	Remote Similarity	NPD8074	Phase 3
0.6957	Remote Similarity	NPD6881	Approved
0.6957	Remote Similarity	NPD6899	Approved
0.6944	Remote Similarity	NPD7748	Approved
0.693	Remote Similarity	NPD6402	Approved
0.693	Remote Similarity	NPD5739	Approved
0.693	Remote Similarity	NPD7128	Approved
0.693	Remote Similarity	NPD6675	Approved
0.6923	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD6650	Approved
0.6917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6009	Approved
0.6916	Remote Similarity	NPD7637	Suspended
0.6909	Remote Similarity	NPD6083	Phase 2
0.6909	Remote Similarity	NPD6084	Phase 2
0.6897	Remote Similarity	NPD6012	Approved
0.6897	Remote Similarity	NPD6014	Approved
0.6897	Remote Similarity	NPD6013	Approved
0.6897	Remote Similarity	NPD6373	Approved
0.6897	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6372	Approved
0.6887	Remote Similarity	NPD1695	Approved
0.6875	Remote Similarity	NPD7260	Phase 2
0.687	Remote Similarity	NPD5701	Approved
0.686	Remote Similarity	NPD7328	Approved
0.686	Remote Similarity	NPD7327	Approved
0.6838	Remote Similarity	NPD7290	Approved
0.6838	Remote Similarity	NPD7102	Approved
0.6838	Remote Similarity	NPD6883	Approved
0.6829	Remote Similarity	NPD8033	Approved
0.6829	Remote Similarity	NPD5983	Phase 2
0.6822	Remote Similarity	NPD6845	Suspended
0.6814	Remote Similarity	NPD5211	Phase 2
0.681	Remote Similarity	NPD7320	Approved
0.681	Remote Similarity	NPD6011	Approved
0.6803	Remote Similarity	NPD7516	Approved
0.6789	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7900	Approved
0.678	Remote Similarity	NPD6847	Approved
0.678	Remote Similarity	NPD6617	Approved
0.678	Remote Similarity	NPD6869	Approved
0.678	Remote Similarity	NPD8130	Phase 1
0.6762	Remote Similarity	NPD3618	Phase 1
0.6762	Remote Similarity	NPD6684	Approved
0.6762	Remote Similarity	NPD7334	Approved
0.6762	Remote Similarity	NPD7146	Approved
0.6762	Remote Similarity	NPD7521	Approved
0.6762	Remote Similarity	NPD6409	Approved
0.6762	Remote Similarity	NPD5330	Approved
0.6759	Remote Similarity	NPD5281	Approved
0.6759	Remote Similarity	NPD5284	Approved
0.6759	Remote Similarity	NPD7515	Phase 2
0.6759	Remote Similarity	NPD6411	Approved
0.6759	Remote Similarity	NPD5693	Phase 1
0.6748	Remote Similarity	NPD8377	Approved
0.6748	Remote Similarity	NPD8294	Approved
0.6727	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6882	Approved
0.672	Remote Similarity	NPD7604	Phase 2
0.6696	Remote Similarity	NPD5141	Approved
0.6694	Remote Similarity	NPD8335	Approved
0.6694	Remote Similarity	NPD8380	Approved
0.6694	Remote Similarity	NPD8296	Approved
0.6694	Remote Similarity	NPD6921	Approved
0.6694	Remote Similarity	NPD8379	Approved
0.6694	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6637	Remote Similarity	NPD4696	Approved
0.6637	Remote Similarity	NPD5285	Approved
0.6637	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD5737	Approved
0.6636	Remote Similarity	NPD6903	Approved
0.6636	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6672	Approved
0.6614	Remote Similarity	NPD6336	Discontinued
0.6607	Remote Similarity	NPD4755	Approved
0.6604	Remote Similarity	NPD4623	Approved
0.6604	Remote Similarity	NPD4519	Discontinued
0.6577	Remote Similarity	NPD5210	Approved
0.6577	Remote Similarity	NPD4629	Approved
0.6574	Remote Similarity	NPD6101	Approved
0.6574	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4753	Phase 2
0.6571	Remote Similarity	NPD3666	Approved
0.6571	Remote Similarity	NPD3133	Approved
0.6571	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3665	Phase 1
0.6557	Remote Similarity	NPD6274	Approved
0.6545	Remote Similarity	NPD4202	Approved
0.6542	Remote Similarity	NPD3573	Approved
0.6542	Remote Similarity	NPD7524	Approved
0.6538	Remote Similarity	NPD5956	Approved
0.6538	Remote Similarity	NPD3667	Approved
0.6522	Remote Similarity	NPD5225	Approved
0.6522	Remote Similarity	NPD4633	Approved
0.6522	Remote Similarity	NPD5224	Approved
0.6522	Remote Similarity	NPD5226	Approved
0.6514	Remote Similarity	NPD5207	Approved
0.6512	Remote Similarity	NPD6033	Approved
0.6505	Remote Similarity	NPD4695	Discontinued
0.65	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4700	Approved
0.6486	Remote Similarity	NPD6001	Approved
0.6466	Remote Similarity	NPD5175	Approved
0.6466	Remote Similarity	NPD5174	Approved
0.6455	Remote Similarity	NPD8035	Phase 2
0.6455	Remote Similarity	NPD8034	Phase 2
0.6455	Remote Similarity	NPD6079	Approved
0.6449	Remote Similarity	NPD4249	Approved
0.6435	Remote Similarity	NPD5223	Approved
0.6429	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6904	Approved
0.6422	Remote Similarity	NPD6673	Approved
0.6422	Remote Similarity	NPD5328	Approved
0.6422	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6051	Approved
0.6422	Remote Similarity	NPD6080	Approved
0.6415	Remote Similarity	NPD4786	Approved
0.6415	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7101	Approved
0.64	Remote Similarity	NPD7100	Approved
0.64	Remote Similarity	NPD4522	Approved
0.6389	Remote Similarity	NPD4251	Approved
0.6389	Remote Similarity	NPD4250	Approved
0.6381	Remote Similarity	NPD5209	Approved
0.6381	Remote Similarity	NPD4221	Approved
0.6381	Remote Similarity	NPD4223	Phase 3
0.6381	Remote Similarity	NPD4269	Approved
0.6381	Remote Similarity	NPD4270	Approved
0.6372	Remote Similarity	NPD5222	Approved
0.6372	Remote Similarity	NPD4697	Phase 3
0.6372	Remote Similarity	NPD5221	Approved
0.6372	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD5692	Phase 3
0.633	Remote Similarity	NPD5208	Approved
0.6328	Remote Similarity	NPD7642	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