NPASS Compound

Structure

NPC159533 OpenBabel07101718192D 22 24 0 0 1 0 0 0 0 0999 V2000 -3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6369 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0029 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 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 -4.1369 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 21 1 0 0 0 0 9 18 2 0 0 0 0 9 22 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 1 0 0 0 13 14 1 0 0 0 0 13 22 1 6 0 0 0 14 16 1 0 0 0 0 14 17 1 6 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 17 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.16
Volume:	312.961
LogP:	2.948
LogD:	2.809
LogS:	-3.348
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.779
Synthetic Accessibility Score:	4.531
Fsp3:	0.706
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:	-4.728
MDCK Permeability:	2.8188211217639036e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	88.8183822631836%
Volume Distribution (VD):	1.059
Pgp-substrate:	22.051469802856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.555
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.473
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	10.929
Half-life (T1/2):	0.39

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.197
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.322
Carcinogencity:	0.845
Eye Corrosion:	0.005
Eye Irritation:	0.024
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC159533

Natural Product ID:	NPC159533
*Common Name:**	Cinnamadin
IUPAC Name:	[(4S,5S,5aS,9aS)-4-hydroxy-6,6,9a-trimethyl-3-oxo-4,5,5a,7,8,9-hexahydro-1H-benzo[e][2]benzofuran-5-yl] acetate
Synonyms:	Cinnamadin
Standard InCHIKey:	IXRCUCMDEOVZLM-QDEZUTFSSA-N
Standard InCHI:	InChI=1S/C17H24O5/c1-9(18)22-13-12(19)11-10(8-21-15(11)20)17(4)7-5-6-16(2,3)14(13)17/h12-14,19H,5-8H2,1-4H3/t12-,13+,14-,17+/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@H](C2=C(COC2=O)[C@@]2(C)CCCC(C)(C)[C@H]12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256914
PubChem CID:	24770036
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
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18179176]
NPO16566	Cinnamosma madagascariensis	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	14.9	%	PMID[532628]

☑ 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 NPC159533 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	223
0.1-0.2	1302
0.2-0.3	4189
0.3-0.4	7167
0.4-0.5	13592
0.5-0.6	7508
0.6-0.7	6506
0.7-0.8	2098
0.8-0.85	97
0.85-0.9	10
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9485	High Similarity	NPC295791
0.91	High Similarity	NPC146731
0.91	High Similarity	NPC296950
0.8922	High Similarity	NPC67321
0.8922	High Similarity	NPC187435
0.89	High Similarity	NPC165250
0.8857	High Similarity	NPC269530
0.8857	High Similarity	NPC42658
0.8846	High Similarity	NPC235014
0.8835	High Similarity	NPC151393
0.8812	High Similarity	NPC99266
0.875	High Similarity	NPC31522
0.8738	High Similarity	NPC112780
0.8738	High Similarity	NPC143609
0.8713	High Similarity	NPC137430
0.8654	High Similarity	NPC325054
0.8654	High Similarity	NPC306265
0.8654	High Similarity	NPC472439
0.8654	High Similarity	NPC469916
0.8654	High Similarity	NPC300614
0.8654	High Similarity	NPC90946
0.8641	High Similarity	NPC111952
0.8627	High Similarity	NPC471208
0.8627	High Similarity	NPC8196
0.8614	High Similarity	NPC97435
0.86	High Similarity	NPC222303
0.8585	High Similarity	NPC317107
0.8571	High Similarity	NPC299590
0.8532	High Similarity	NPC53396
0.8532	High Similarity	NPC469684
0.8532	High Similarity	NPC98249
0.8529	High Similarity	NPC476081
0.8515	High Similarity	NPC476299
0.8515	High Similarity	NPC474012
0.8505	High Similarity	NPC317687
0.85	High Similarity	NPC175351
0.85	High Similarity	NPC121402
0.85	High Similarity	NPC132753
0.85	High Similarity	NPC474395
0.85	High Similarity	NPC151681
0.85	High Similarity	NPC224356
0.8491	Intermediate Similarity	NPC5103
0.8455	Intermediate Similarity	NPC284707
0.8447	Intermediate Similarity	NPC99510
0.8447	Intermediate Similarity	NPC72842
0.8431	Intermediate Similarity	NPC308824
0.8431	Intermediate Similarity	NPC303559
0.8416	Intermediate Similarity	NPC216478
0.8416	Intermediate Similarity	NPC159763
0.8416	Intermediate Similarity	NPC278386
0.8416	Intermediate Similarity	NPC124512
0.8411	Intermediate Similarity	NPC324683
0.84	Intermediate Similarity	NPC472363
0.84	Intermediate Similarity	NPC242848
0.84	Intermediate Similarity	NPC472362
0.84	Intermediate Similarity	NPC240673
0.84	Intermediate Similarity	NPC17578
0.84	Intermediate Similarity	NPC134072
0.84	Intermediate Similarity	NPC234993
0.84	Intermediate Similarity	NPC154526
0.8393	Intermediate Similarity	NPC67569
0.8384	Intermediate Similarity	NPC474555
0.8365	Intermediate Similarity	NPC258532
0.8364	Intermediate Similarity	NPC58662
0.835	Intermediate Similarity	NPC472552
0.835	Intermediate Similarity	NPC273005
0.835	Intermediate Similarity	NPC31058
0.835	Intermediate Similarity	NPC58329
0.835	Intermediate Similarity	NPC469606
0.8333	Intermediate Similarity	NPC476801
0.8333	Intermediate Similarity	NPC47024
0.8333	Intermediate Similarity	NPC38855
0.8333	Intermediate Similarity	NPC472002
0.8319	Intermediate Similarity	NPC23786
0.8319	Intermediate Similarity	NPC470265
0.8318	Intermediate Similarity	NPC478211
0.8317	Intermediate Similarity	NPC199099
0.8304	Intermediate Similarity	NPC268530
0.8304	Intermediate Similarity	NPC154491
0.8302	Intermediate Similarity	NPC322903
0.8302	Intermediate Similarity	NPC37628
0.83	Intermediate Similarity	NPC111273
0.8288	Intermediate Similarity	NPC478205
0.8288	Intermediate Similarity	NPC108581
0.8288	Intermediate Similarity	NPC240509
0.8288	Intermediate Similarity	NPC478206
0.8286	Intermediate Similarity	NPC469607
0.8283	Intermediate Similarity	NPC110022
0.8283	Intermediate Similarity	NPC472641
0.8283	Intermediate Similarity	NPC472640
0.8283	Intermediate Similarity	NPC115021
0.8269	Intermediate Similarity	NPC474822
0.8269	Intermediate Similarity	NPC120321
0.8269	Intermediate Similarity	NPC156681
0.8269	Intermediate Similarity	NPC474165
0.8269	Intermediate Similarity	NPC69171
0.8265	Intermediate Similarity	NPC472307
0.8257	Intermediate Similarity	NPC469463
0.8257	Intermediate Similarity	NPC469454
0.8257	Intermediate Similarity	NPC478212
0.8257	Intermediate Similarity	NPC469496
0.8252	Intermediate Similarity	NPC472554
0.8246	Intermediate Similarity	NPC67251
0.8246	Intermediate Similarity	NPC469789
0.8241	Intermediate Similarity	NPC474846
0.8241	Intermediate Similarity	NPC469655
0.8241	Intermediate Similarity	NPC100329
0.8241	Intermediate Similarity	NPC179798
0.8241	Intermediate Similarity	NPC188738
0.8241	Intermediate Similarity	NPC132790
0.8241	Intermediate Similarity	NPC469656
0.8241	Intermediate Similarity	NPC97939
0.8241	Intermediate Similarity	NPC304180
0.8241	Intermediate Similarity	NPC247031
0.823	Intermediate Similarity	NPC4021
0.823	Intermediate Similarity	NPC476204
0.823	Intermediate Similarity	NPC170084
0.823	Intermediate Similarity	NPC159456
0.823	Intermediate Similarity	NPC129434
0.8229	Intermediate Similarity	NPC250981
0.8224	Intermediate Similarity	NPC42662
0.8224	Intermediate Similarity	NPC474243
0.8218	Intermediate Similarity	NPC165632
0.8218	Intermediate Similarity	NPC202833
0.8214	Intermediate Similarity	NPC230513
0.8208	Intermediate Similarity	NPC78966
0.8208	Intermediate Similarity	NPC284732
0.8208	Intermediate Similarity	NPC230541
0.82	Intermediate Similarity	NPC474554
0.8198	Intermediate Similarity	NPC478204
0.8198	Intermediate Similarity	NPC475323
0.8198	Intermediate Similarity	NPC473656
0.8198	Intermediate Similarity	NPC473968
0.8198	Intermediate Similarity	NPC55296
0.8198	Intermediate Similarity	NPC474483
0.819	Intermediate Similarity	NPC283850
0.819	Intermediate Similarity	NPC161775
0.8182	Intermediate Similarity	NPC110861
0.8182	Intermediate Similarity	NPC117712
0.8173	Intermediate Similarity	NPC80781
0.8173	Intermediate Similarity	NPC164551
0.8173	Intermediate Similarity	NPC183571
0.8165	Intermediate Similarity	NPC470063
0.8158	Intermediate Similarity	NPC269642
0.8155	Intermediate Similarity	NPC198880
0.8148	Intermediate Similarity	NPC478209
0.8148	Intermediate Similarity	NPC472666
0.8142	Intermediate Similarity	NPC251226
0.8137	Intermediate Similarity	NPC91695
0.8137	Intermediate Similarity	NPC70145
0.8137	Intermediate Similarity	NPC73911
0.8137	Intermediate Similarity	NPC205143
0.8131	Intermediate Similarity	NPC189075
0.8131	Intermediate Similarity	NPC476802
0.8131	Intermediate Similarity	NPC89171
0.8131	Intermediate Similarity	NPC94377
0.8131	Intermediate Similarity	NPC275539
0.8125	Intermediate Similarity	NPC50774
0.8125	Intermediate Similarity	NPC251310
0.8125	Intermediate Similarity	NPC709
0.8125	Intermediate Similarity	NPC186525
0.8119	Intermediate Similarity	NPC183012
0.8119	Intermediate Similarity	NPC471786
0.8119	Intermediate Similarity	NPC157686
0.8119	Intermediate Similarity	NPC259042
0.8119	Intermediate Similarity	NPC37603
0.8113	Intermediate Similarity	NPC34768
0.8113	Intermediate Similarity	NPC477125
0.8113	Intermediate Similarity	NPC181357
0.8113	Intermediate Similarity	NPC102352
0.8108	Intermediate Similarity	NPC44170
0.8108	Intermediate Similarity	NPC64318
0.8108	Intermediate Similarity	NPC268954
0.8103	Intermediate Similarity	NPC293112
0.81	Intermediate Similarity	NPC139692
0.81	Intermediate Similarity	NPC53555
0.81	Intermediate Similarity	NPC99653
0.8095	Intermediate Similarity	NPC61442
0.8095	Intermediate Similarity	NPC23584
0.8095	Intermediate Similarity	NPC95899
0.8091	Intermediate Similarity	NPC471204
0.8091	Intermediate Similarity	NPC475966
0.8091	Intermediate Similarity	NPC25909
0.8091	Intermediate Similarity	NPC477126
0.8091	Intermediate Similarity	NPC56448
0.8091	Intermediate Similarity	NPC264153
0.8081	Intermediate Similarity	NPC472642
0.8077	Intermediate Similarity	NPC111292
0.8077	Intermediate Similarity	NPC471412
0.8077	Intermediate Similarity	NPC471075
0.8077	Intermediate Similarity	NPC242666
0.807	Intermediate Similarity	NPC46570
0.8058	Intermediate Similarity	NPC316598
0.8058	Intermediate Similarity	NPC23364
0.8056	Intermediate Similarity	NPC472216
0.8056	Intermediate Similarity	NPC475065
0.8056	Intermediate Similarity	NPC141350
0.8056	Intermediate Similarity	NPC284828
0.8056	Intermediate Similarity	NPC273433
0.8056	Intermediate Similarity	NPC87335

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 NPC159533 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1806
0.2-0.3	3551
0.3-0.4	2221
0.4-0.5	850
0.5-0.6	344
0.6-0.7	166
0.7-0.8	17
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD4061	Clinical (unspecified phase)
0.8416	Intermediate Similarity	NPD4225	Approved
0.8318	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7115	Discovery
0.781	Intermediate Similarity	NPD7639	Approved
0.781	Intermediate Similarity	NPD7640	Approved
0.7798	Intermediate Similarity	NPD6686	Approved
0.7714	Intermediate Similarity	NPD7638	Approved
0.7664	Intermediate Similarity	NPD7632	Discontinued
0.75	Intermediate Similarity	NPD6371	Approved
0.7477	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7319	Approved
0.7414	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD46	Approved
0.7379	Intermediate Similarity	NPD6698	Approved
0.7373	Intermediate Similarity	NPD6319	Approved
0.7355	Intermediate Similarity	NPD7507	Approved
0.7248	Intermediate Similarity	NPD5344	Discontinued
0.7238	Intermediate Similarity	NPD5778	Approved
0.7238	Intermediate Similarity	NPD5779	Approved
0.7228	Intermediate Similarity	NPD1694	Approved
0.719	Intermediate Similarity	NPD8328	Phase 3
0.7167	Intermediate Similarity	NPD8515	Approved
0.7167	Intermediate Similarity	NPD8517	Approved
0.7167	Intermediate Similarity	NPD8513	Phase 3
0.7167	Intermediate Similarity	NPD8516	Approved
0.7155	Intermediate Similarity	NPD4632	Approved
0.713	Intermediate Similarity	NPD7902	Approved
0.71	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6412	Phase 2
0.708	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6399	Phase 3
0.7059	Intermediate Similarity	NPD7328	Approved
0.7059	Intermediate Similarity	NPD7327	Approved
0.7025	Intermediate Similarity	NPD8033	Approved
0.7009	Intermediate Similarity	NPD7748	Approved
0.7	Intermediate Similarity	NPD7516	Approved
0.6992	Remote Similarity	NPD7492	Approved
0.6991	Remote Similarity	NPD7128	Approved
0.6991	Remote Similarity	NPD6675	Approved
0.6991	Remote Similarity	NPD6402	Approved
0.6991	Remote Similarity	NPD5739	Approved
0.6991	Remote Similarity	NPD6008	Approved
0.699	Remote Similarity	NPD3618	Phase 1
0.6981	Remote Similarity	NPD7515	Phase 2
0.6981	Remote Similarity	NPD7983	Approved
0.6957	Remote Similarity	NPD6372	Approved
0.6957	Remote Similarity	NPD6373	Approved
0.6944	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6054	Approved
0.6942	Remote Similarity	NPD8294	Approved
0.6942	Remote Similarity	NPD6059	Approved
0.6942	Remote Similarity	NPD8377	Approved
0.6935	Remote Similarity	NPD6616	Approved
0.693	Remote Similarity	NPD5701	Approved
0.693	Remote Similarity	NPD5697	Approved
0.6923	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD8297	Approved
0.6897	Remote Similarity	NPD4634	Approved
0.6887	Remote Similarity	NPD5785	Approved
0.6885	Remote Similarity	NPD8335	Approved
0.6885	Remote Similarity	NPD8378	Approved
0.6885	Remote Similarity	NPD6016	Approved
0.6885	Remote Similarity	NPD8296	Approved
0.6885	Remote Similarity	NPD8380	Approved
0.6885	Remote Similarity	NPD8379	Approved
0.6885	Remote Similarity	NPD6015	Approved
0.688	Remote Similarity	NPD8074	Phase 3
0.688	Remote Similarity	NPD8293	Discontinued
0.688	Remote Similarity	NPD7078	Approved
0.687	Remote Similarity	NPD6899	Approved
0.687	Remote Similarity	NPD6881	Approved
0.687	Remote Similarity	NPD7320	Approved
0.6864	Remote Similarity	NPD8133	Approved
0.6852	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7900	Approved
0.6847	Remote Similarity	NPD6648	Approved
0.6838	Remote Similarity	NPD6650	Approved
0.6838	Remote Similarity	NPD6649	Approved
0.6833	Remote Similarity	NPD6009	Approved
0.6829	Remote Similarity	NPD6370	Approved
0.6829	Remote Similarity	NPD5988	Approved
0.6825	Remote Similarity	NPD7736	Approved
0.6822	Remote Similarity	NPD6411	Approved
0.6822	Remote Similarity	NPD7637	Suspended
0.681	Remote Similarity	NPD6014	Approved
0.681	Remote Similarity	NPD6013	Approved
0.681	Remote Similarity	NPD6012	Approved
0.6752	Remote Similarity	NPD6883	Approved
0.6752	Remote Similarity	NPD7290	Approved
0.6752	Remote Similarity	NPD7102	Approved
0.6748	Remote Similarity	NPD5983	Phase 2
0.6748	Remote Similarity	NPD7503	Approved
0.6748	Remote Similarity	NPD6921	Approved
0.6729	Remote Similarity	NPD7838	Discovery
0.6726	Remote Similarity	NPD5211	Phase 2
0.6724	Remote Similarity	NPD6011	Approved
0.6697	Remote Similarity	NPD5282	Discontinued
0.6695	Remote Similarity	NPD6847	Approved
0.6695	Remote Similarity	NPD6617	Approved
0.6695	Remote Similarity	NPD6869	Approved
0.6695	Remote Similarity	NPD8130	Phase 1
0.6695	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7604	Phase 2
0.6639	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD5695	Phase 3
0.6636	Remote Similarity	NPD5328	Approved
0.6635	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5141	Approved
0.6607	Remote Similarity	NPD5696	Approved
0.6607	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4202	Approved
0.6602	Remote Similarity	NPD3667	Approved
0.6577	Remote Similarity	NPD4697	Phase 3
0.6555	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4700	Approved
0.6549	Remote Similarity	NPD5285	Approved
0.6549	Remote Similarity	NPD4696	Approved
0.6549	Remote Similarity	NPD5286	Approved
0.6538	Remote Similarity	NPD7260	Phase 2
0.6535	Remote Similarity	NPD6336	Discontinued
0.6514	Remote Similarity	NPD6079	Approved
0.6509	Remote Similarity	NPD7334	Approved
0.6509	Remote Similarity	NPD7521	Approved
0.6509	Remote Similarity	NPD5330	Approved
0.6509	Remote Similarity	NPD7146	Approved
0.6509	Remote Similarity	NPD6684	Approved
0.6509	Remote Similarity	NPD6409	Approved
0.6489	Remote Similarity	NPD6845	Suspended
0.6476	Remote Similarity	NPD4786	Approved
0.6476	Remote Similarity	NPD3133	Approved
0.6476	Remote Similarity	NPD3666	Approved
0.6476	Remote Similarity	NPD3665	Phase 1
0.6475	Remote Similarity	NPD6274	Approved
0.6435	Remote Similarity	NPD5226	Approved
0.6435	Remote Similarity	NPD5225	Approved
0.6435	Remote Similarity	NPD4633	Approved
0.6435	Remote Similarity	NPD5224	Approved
0.6434	Remote Similarity	NPD6033	Approved
0.6429	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5222	Approved
0.6429	Remote Similarity	NPD5221	Approved
0.6415	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5363	Approved
0.6389	Remote Similarity	NPD6903	Approved
0.6389	Remote Similarity	NPD5737	Approved
0.6389	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6672	Approved
0.6379	Remote Similarity	NPD5175	Approved
0.6379	Remote Similarity	NPD5174	Approved
0.6378	Remote Similarity	NPD6067	Discontinued
0.6373	Remote Similarity	NPD6697	Approved
0.6373	Remote Similarity	NPD6115	Approved
0.6373	Remote Similarity	NPD6118	Approved
0.6373	Remote Similarity	NPD6114	Approved
0.6372	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD5693	Phase 1
0.6364	Remote Similarity	NPD5281	Approved
0.6348	Remote Similarity	NPD4159	Approved
0.6348	Remote Similarity	NPD5223	Approved
0.6339	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4753	Phase 2
0.632	Remote Similarity	NPD7100	Approved
0.632	Remote Similarity	NPD7101	Approved
0.6296	Remote Similarity	NPD3573	Approved
0.6296	Remote Similarity	NPD7524	Approved
0.629	Remote Similarity	NPD6317	Approved
0.6286	Remote Similarity	NPD4269	Approved
0.6286	Remote Similarity	NPD4270	Approved
0.6275	Remote Similarity	NPD6116	Phase 1
0.6271	Remote Similarity	NPD4767	Approved
0.6271	Remote Similarity	NPD4768	Approved
0.6262	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6335	Approved
0.624	Remote Similarity	NPD6313	Approved
0.624	Remote Similarity	NPD6314	Approved
0.6239	Remote Similarity	NPD4754	Approved
0.6226	Remote Similarity	NPD7154	Phase 3
0.622	Remote Similarity	NPD6909	Approved
0.622	Remote Similarity	NPD6908	Approved
0.622	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD3617	Approved
0.621	Remote Similarity	NPD6868	Approved
0.6207	Remote Similarity	NPD1700	Approved
0.6204	Remote Similarity	NPD5786	Approved
0.6204	Remote Similarity	NPD4249	Approved
0.6204	Remote Similarity	NPD5279	Phase 3
0.6204	Remote Similarity	NPD4519	Discontinued
0.6204	Remote Similarity	NPD4623	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