NPASS Compound

Structure

NPC295791 OpenBabel07101719142D 22 24 0 0 1 0 0 0 0 0999 V2000 -5.0029 0.5000 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 -4.6369 0.1340 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 -5.0029 -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 -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 -5.8690 -1.0000 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 12 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 6 0 0 0 13 14 1 0 0 0 0 13 22 1 1 0 0 0 14 16 1 0 0 0 0 14 17 1 1 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 17 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.16
Volume:	312.961
LogP:	3.005
LogD:	2.784
LogS:	-3.383
# 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:	4.467
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:	-4.777
MDCK Permeability:	2.4672104700584896e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.648
Plasma Protein Binding (PPB):	86.39081573486328%
Volume Distribution (VD):	1.013
Pgp-substrate:	28.928735733032227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.411
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.59
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.249
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	9.102
Half-life (T1/2):	0.485

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.275
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.308
Carcinogencity:	0.861
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC295791

Natural Product ID:	NPC295791
*Common Name:**	Ugandensolide
IUPAC Name:	[(4S,5S,5aS,9aS)-4-hydroxy-6,6,9a-trimethyl-1-oxo-4,5,5a,7,8,9-hexahydro-3H-benzo[e][2]benzofuran-5-yl] acetate
Synonyms:	Ugandensolide
Standard InCHIKey:	NYFWOFCJTJKPJY-QDEZUTFSSA-N
Standard InCHI:	InChI=1S/C17H24O5/c1-9(18)22-13-12(19)10-8-21-15(20)11(10)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(C(=O)OC2)[C@@]2(C)CCCC(C)(C)[C@H]12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256710
PubChem CID:	12444581
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]
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]

☑ 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	=	46.2	%	PMID[502753]

☑ 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 NPC295791 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	218
0.1-0.2	1293
0.2-0.3	4185
0.3-0.4	7117
0.4-0.5	13625
0.5-0.6	7552
0.6-0.7	6472
0.7-0.8	2140
0.8-0.85	82
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9485	High Similarity	NPC159533
0.8824	High Similarity	NPC187435
0.8824	High Similarity	NPC67321
0.88	High Similarity	NPC165250
0.8762	High Similarity	NPC269530
0.875	High Similarity	NPC5103
0.8725	High Similarity	NPC111952
0.8713	High Similarity	NPC99266
0.8687	High Similarity	NPC222303
0.8654	High Similarity	NPC299590
0.8641	High Similarity	NPC143609
0.8641	High Similarity	NPC112780
0.8627	High Similarity	NPC258532
0.8627	High Similarity	NPC146731
0.8627	High Similarity	NPC296950
0.8614	High Similarity	NPC137430
0.8611	High Similarity	NPC473968
0.8585	High Similarity	NPC42658
0.8585	High Similarity	NPC472002
0.8571	High Similarity	NPC478211
0.8558	High Similarity	NPC325054
0.8558	High Similarity	NPC472439
0.8558	High Similarity	NPC306265
0.8558	High Similarity	NPC469916
0.8544	High Similarity	NPC469607
0.8529	High Similarity	NPC8196
0.8529	High Similarity	NPC471208
0.8515	High Similarity	NPC97435
0.8515	High Similarity	NPC471412
0.8505	High Similarity	NPC469496
0.8505	High Similarity	NPC469463
0.8505	High Similarity	NPC469454
0.8491	Intermediate Similarity	NPC474846
0.8491	Intermediate Similarity	NPC132790
0.8491	Intermediate Similarity	NPC469655
0.8491	Intermediate Similarity	NPC304180
0.8491	Intermediate Similarity	NPC97939
0.8491	Intermediate Similarity	NPC247031
0.8491	Intermediate Similarity	NPC100329
0.8491	Intermediate Similarity	NPC188738
0.8491	Intermediate Similarity	NPC469656
0.8491	Intermediate Similarity	NPC179798
0.8485	Intermediate Similarity	NPC134072
0.8485	Intermediate Similarity	NPC234993
0.8476	Intermediate Similarity	NPC472534
0.8476	Intermediate Similarity	NPC143706
0.8476	Intermediate Similarity	NPC31522
0.8462	Intermediate Similarity	NPC230541
0.844	Intermediate Similarity	NPC53396
0.844	Intermediate Similarity	NPC469684
0.844	Intermediate Similarity	NPC98249
0.8431	Intermediate Similarity	NPC476081
0.8431	Intermediate Similarity	NPC162973
0.8431	Intermediate Similarity	NPC472552
0.8426	Intermediate Similarity	NPC178289
0.8416	Intermediate Similarity	NPC471413
0.8416	Intermediate Similarity	NPC38855
0.84	Intermediate Similarity	NPC175351
0.84	Intermediate Similarity	NPC121402
0.84	Intermediate Similarity	NPC132753
0.84	Intermediate Similarity	NPC151681
0.84	Intermediate Similarity	NPC224356
0.8396	Intermediate Similarity	NPC235014
0.8381	Intermediate Similarity	NPC300614
0.8381	Intermediate Similarity	NPC275539
0.8381	Intermediate Similarity	NPC189075
0.8381	Intermediate Similarity	NPC90946
0.8381	Intermediate Similarity	NPC151393
0.8367	Intermediate Similarity	NPC472641
0.8367	Intermediate Similarity	NPC472640
0.8367	Intermediate Similarity	NPC110022
0.8365	Intermediate Similarity	NPC181357
0.8365	Intermediate Similarity	NPC102352
0.8364	Intermediate Similarity	NPC284707
0.8351	Intermediate Similarity	NPC472307
0.835	Intermediate Similarity	NPC474822
0.8349	Intermediate Similarity	NPC106228
0.8349	Intermediate Similarity	NPC471816
0.8349	Intermediate Similarity	NPC138372
0.8333	Intermediate Similarity	NPC475966
0.8333	Intermediate Similarity	NPC303559
0.8333	Intermediate Similarity	NPC56448
0.8333	Intermediate Similarity	NPC472554
0.8333	Intermediate Similarity	NPC51978
0.8333	Intermediate Similarity	NPC25909
0.8333	Intermediate Similarity	NPC471204
0.8317	Intermediate Similarity	NPC23364
0.8317	Intermediate Similarity	NPC216478
0.8302	Intermediate Similarity	NPC478210
0.8302	Intermediate Similarity	NPC141350
0.8302	Intermediate Similarity	NPC273433
0.83	Intermediate Similarity	NPC472363
0.83	Intermediate Similarity	NPC165632
0.83	Intermediate Similarity	NPC202833
0.83	Intermediate Similarity	NPC472362
0.83	Intermediate Similarity	NPC154526
0.8288	Intermediate Similarity	NPC475775
0.8288	Intermediate Similarity	NPC475041
0.8288	Intermediate Similarity	NPC476529
0.8286	Intermediate Similarity	NPC144854
0.8286	Intermediate Similarity	NPC3316
0.8286	Intermediate Similarity	NPC110496
0.8283	Intermediate Similarity	NPC474554
0.8283	Intermediate Similarity	NPC250075
0.8273	Intermediate Similarity	NPC58662
0.8273	Intermediate Similarity	NPC13713
0.8269	Intermediate Similarity	NPC65523
0.8252	Intermediate Similarity	NPC31058
0.8252	Intermediate Similarity	NPC58329
0.8252	Intermediate Similarity	NPC273005
0.8252	Intermediate Similarity	NPC469606
0.8241	Intermediate Similarity	NPC470063
0.8241	Intermediate Similarity	NPC476801
0.8241	Intermediate Similarity	NPC302146
0.8235	Intermediate Similarity	NPC47024
0.8235	Intermediate Similarity	NPC476767
0.8235	Intermediate Similarity	NPC476299
0.8235	Intermediate Similarity	NPC472644
0.8235	Intermediate Similarity	NPC474012
0.8218	Intermediate Similarity	NPC205143
0.8214	Intermediate Similarity	NPC107338
0.8214	Intermediate Similarity	NPC109607
0.8214	Intermediate Similarity	NPC268530
0.8214	Intermediate Similarity	NPC154491
0.8208	Intermediate Similarity	NPC277017
0.8208	Intermediate Similarity	NPC37628
0.8208	Intermediate Similarity	NPC476479
0.8208	Intermediate Similarity	NPC154608
0.8208	Intermediate Similarity	NPC192813
0.8208	Intermediate Similarity	NPC293850
0.8198	Intermediate Similarity	NPC108581
0.8198	Intermediate Similarity	NPC478206
0.8198	Intermediate Similarity	NPC240509
0.8198	Intermediate Similarity	NPC478205
0.819	Intermediate Similarity	NPC127609
0.819	Intermediate Similarity	NPC323834
0.819	Intermediate Similarity	NPC478208
0.8182	Intermediate Similarity	NPC176840
0.8182	Intermediate Similarity	NPC139692
0.8182	Intermediate Similarity	NPC99653
0.8182	Intermediate Similarity	NPC477436
0.8182	Intermediate Similarity	NPC477435
0.8182	Intermediate Similarity	NPC53555
0.8182	Intermediate Similarity	NPC478216
0.8173	Intermediate Similarity	NPC120321
0.8173	Intermediate Similarity	NPC23584
0.8165	Intermediate Similarity	NPC478212
0.8163	Intermediate Similarity	NPC472642
0.8158	Intermediate Similarity	NPC469789
0.8158	Intermediate Similarity	NPC67251
0.8155	Intermediate Similarity	NPC472643
0.8148	Intermediate Similarity	NPC317107
0.8148	Intermediate Similarity	NPC201992
0.8148	Intermediate Similarity	NPC324683
0.8142	Intermediate Similarity	NPC46570
0.8142	Intermediate Similarity	NPC4021
0.8142	Intermediate Similarity	NPC159456
0.8131	Intermediate Similarity	NPC472216
0.8131	Intermediate Similarity	NPC284828
0.8131	Intermediate Similarity	NPC173905
0.8131	Intermediate Similarity	NPC469370
0.8131	Intermediate Similarity	NPC5475
0.8131	Intermediate Similarity	NPC474243
0.8125	Intermediate Similarity	NPC473636
0.8125	Intermediate Similarity	NPC469380
0.8125	Intermediate Similarity	NPC230513
0.8125	Intermediate Similarity	NPC19028
0.8125	Intermediate Similarity	NPC9674
0.8125	Intermediate Similarity	NPC250981
0.8125	Intermediate Similarity	NPC122971
0.8125	Intermediate Similarity	NPC77689
0.8119	Intermediate Similarity	NPC17578
0.8119	Intermediate Similarity	NPC284194
0.8119	Intermediate Similarity	NPC240673
0.8119	Intermediate Similarity	NPC471765
0.8119	Intermediate Similarity	NPC221801
0.8119	Intermediate Similarity	NPC29952
0.8119	Intermediate Similarity	NPC211810
0.8119	Intermediate Similarity	NPC7124
0.8119	Intermediate Similarity	NPC242848
0.8119	Intermediate Similarity	NPC129569
0.8113	Intermediate Similarity	NPC471783
0.8113	Intermediate Similarity	NPC78966
0.8113	Intermediate Similarity	NPC473165
0.8113	Intermediate Similarity	NPC469318
0.8113	Intermediate Similarity	NPC9457
0.8113	Intermediate Similarity	NPC284732
0.8113	Intermediate Similarity	NPC473173
0.8113	Intermediate Similarity	NPC180744
0.8108	Intermediate Similarity	NPC23046
0.8108	Intermediate Similarity	NPC284068
0.8108	Intermediate Similarity	NPC478204
0.8108	Intermediate Similarity	NPC55296
0.8108	Intermediate Similarity	NPC473590
0.8108	Intermediate Similarity	NPC134430
0.81	Intermediate Similarity	NPC472416
0.81	Intermediate Similarity	NPC105375
0.81	Intermediate Similarity	NPC196227
0.81	Intermediate Similarity	NPC474555
0.81	Intermediate Similarity	NPC182826

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 NPC295791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1766
0.2-0.3	3583
0.3-0.4	2253
0.4-0.5	836
0.5-0.6	318
0.6-0.7	186
0.7-0.8	16
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
0.8654	High Similarity	NPD4061	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD4225	Approved
0.7944	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7640	Approved
0.7885	Intermediate Similarity	NPD7639	Approved
0.787	Intermediate Similarity	NPD6686	Approved
0.7788	Intermediate Similarity	NPD7638	Approved
0.7736	Intermediate Similarity	NPD7632	Discontinued
0.7712	Intermediate Similarity	NPD7507	Approved
0.7632	Intermediate Similarity	NPD7115	Discovery
0.7522	Intermediate Similarity	NPD4632	Approved
0.7521	Intermediate Similarity	NPD7319	Approved
0.7451	Intermediate Similarity	NPD6698	Approved
0.7451	Intermediate Similarity	NPD46	Approved
0.7436	Intermediate Similarity	NPD6319	Approved
0.7387	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6402	Approved
0.7364	Intermediate Similarity	NPD7128	Approved
0.7364	Intermediate Similarity	NPD5739	Approved
0.7364	Intermediate Similarity	NPD6675	Approved
0.7328	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5344	Discontinued
0.7308	Intermediate Similarity	NPD5778	Approved
0.7308	Intermediate Similarity	NPD5779	Approved
0.7297	Intermediate Similarity	NPD5697	Approved
0.7297	Intermediate Similarity	NPD5701	Approved
0.7281	Intermediate Similarity	NPD6053	Discontinued
0.7281	Intermediate Similarity	NPD8297	Approved
0.7232	Intermediate Similarity	NPD6881	Approved
0.7232	Intermediate Similarity	NPD7320	Approved
0.7232	Intermediate Similarity	NPD6899	Approved
0.7207	Intermediate Similarity	NPD6008	Approved
0.7179	Intermediate Similarity	NPD6009	Approved
0.7172	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6013	Approved
0.7168	Intermediate Similarity	NPD6012	Approved
0.7168	Intermediate Similarity	NPD6373	Approved
0.7168	Intermediate Similarity	NPD6372	Approved
0.7168	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7129	Intermediate Similarity	NPD1694	Approved
0.7119	Intermediate Similarity	NPD7328	Approved
0.7119	Intermediate Similarity	NPD7327	Approved
0.7107	Intermediate Similarity	NPD8328	Phase 3
0.7105	Intermediate Similarity	NPD6883	Approved
0.7105	Intermediate Similarity	NPD7290	Approved
0.7105	Intermediate Similarity	NPD7102	Approved
0.7105	Intermediate Similarity	NPD6371	Approved
0.7091	Intermediate Similarity	NPD5211	Phase 2
0.7083	Intermediate Similarity	NPD5983	Phase 2
0.7083	Intermediate Similarity	NPD8517	Approved
0.7083	Intermediate Similarity	NPD8516	Approved
0.7083	Intermediate Similarity	NPD8033	Approved
0.7083	Intermediate Similarity	NPD8515	Approved
0.7083	Intermediate Similarity	NPD8513	Phase 3
0.708	Intermediate Similarity	NPD6011	Approved
0.7075	Intermediate Similarity	NPD7748	Approved
0.7059	Intermediate Similarity	NPD7516	Approved
0.7049	Intermediate Similarity	NPD7492	Approved
0.7048	Intermediate Similarity	NPD7983	Approved
0.7048	Intermediate Similarity	NPD7515	Phase 2
0.7043	Intermediate Similarity	NPD6869	Approved
0.7043	Intermediate Similarity	NPD6650	Approved
0.7043	Intermediate Similarity	NPD6847	Approved
0.7043	Intermediate Similarity	NPD6649	Approved
0.7043	Intermediate Similarity	NPD8130	Phase 1
0.7043	Intermediate Similarity	NPD6617	Approved
0.7037	Intermediate Similarity	NPD4755	Approved
0.7037	Intermediate Similarity	NPD7902	Approved
0.7019	Intermediate Similarity	NPD5328	Approved
0.7	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD8377	Approved
0.7	Intermediate Similarity	NPD6054	Approved
0.7	Intermediate Similarity	NPD8294	Approved
0.6992	Remote Similarity	NPD6616	Approved
0.6983	Remote Similarity	NPD6882	Approved
0.6981	Remote Similarity	NPD6399	Phase 3
0.6967	Remote Similarity	NPD7604	Phase 2
0.6964	Remote Similarity	NPD5141	Approved
0.6957	Remote Similarity	NPD4634	Approved
0.6942	Remote Similarity	NPD6016	Approved
0.6942	Remote Similarity	NPD8378	Approved
0.6942	Remote Similarity	NPD6015	Approved
0.6942	Remote Similarity	NPD8335	Approved
0.6942	Remote Similarity	NPD8380	Approved
0.6942	Remote Similarity	NPD8379	Approved
0.6942	Remote Similarity	NPD8296	Approved
0.6935	Remote Similarity	NPD8293	Discontinued
0.6935	Remote Similarity	NPD7078	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.6909	Remote Similarity	NPD4696	Approved
0.6909	Remote Similarity	NPD5285	Approved
0.6909	Remote Similarity	NPD6648	Approved
0.6909	Remote Similarity	NPD5286	Approved
0.6909	Remote Similarity	NPD4700	Approved
0.6897	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3618	Phase 1
0.6887	Remote Similarity	NPD6079	Approved
0.6887	Remote Similarity	NPD6411	Approved
0.6885	Remote Similarity	NPD5988	Approved
0.6885	Remote Similarity	NPD6370	Approved
0.688	Remote Similarity	NPD7736	Approved
0.6855	Remote Similarity	NPD6336	Discontinued
0.6852	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6274	Approved
0.6803	Remote Similarity	NPD7503	Approved
0.68	Remote Similarity	NPD8074	Phase 3
0.6792	Remote Similarity	NPD7838	Discovery
0.6789	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5222	Approved
0.6789	Remote Similarity	NPD4697	Phase 3
0.6789	Remote Similarity	NPD5221	Approved
0.6786	Remote Similarity	NPD5224	Approved
0.6786	Remote Similarity	NPD5226	Approved
0.6786	Remote Similarity	NPD4633	Approved
0.6786	Remote Similarity	NPD5225	Approved
0.6759	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7900	Approved
0.6727	Remote Similarity	NPD6084	Phase 2
0.6727	Remote Similarity	NPD6083	Phase 2
0.6727	Remote Similarity	NPD5173	Approved
0.6726	Remote Similarity	NPD5174	Approved
0.6726	Remote Similarity	NPD5175	Approved
0.6719	Remote Similarity	NPD7260	Phase 2
0.6699	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6101	Approved
0.6697	Remote Similarity	NPD5695	Phase 3
0.6696	Remote Similarity	NPD5223	Approved
0.6696	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6612	Remote Similarity	NPD6317	Approved
0.661	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4768	Approved
0.6609	Remote Similarity	NPD4767	Approved
0.6579	Remote Similarity	NPD4754	Approved
0.6574	Remote Similarity	NPD8035	Phase 2
0.6574	Remote Similarity	NPD7637	Suspended
0.6574	Remote Similarity	NPD8034	Phase 2
0.6571	Remote Similarity	NPD6684	Approved
0.6571	Remote Similarity	NPD7334	Approved
0.6571	Remote Similarity	NPD6409	Approved
0.6571	Remote Similarity	NPD7146	Approved
0.6571	Remote Similarity	NPD5330	Approved
0.6571	Remote Similarity	NPD7521	Approved
0.6557	Remote Similarity	NPD6335	Approved
0.6557	Remote Similarity	NPD6313	Approved
0.6557	Remote Similarity	NPD6314	Approved
0.6538	Remote Similarity	NPD4786	Approved
0.6538	Remote Similarity	NPD3666	Approved
0.6538	Remote Similarity	NPD3133	Approved
0.6538	Remote Similarity	NPD3665	Phase 1
0.6532	Remote Similarity	NPD6909	Approved
0.6532	Remote Similarity	NPD6908	Approved
0.6529	Remote Similarity	NPD6868	Approved
0.6518	Remote Similarity	NPD5696	Approved
0.6518	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4730	Approved
0.6496	Remote Similarity	NPD4729	Approved
0.6496	Remote Similarity	NPD5128	Approved
0.6484	Remote Similarity	NPD6033	Approved
0.6481	Remote Similarity	NPD5785	Approved
0.6476	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6672	Approved
0.6449	Remote Similarity	NPD6903	Approved
0.6449	Remote Similarity	NPD5737	Approved
0.6436	Remote Similarity	NPD6697	Approved
0.6436	Remote Similarity	NPD6115	Approved
0.6436	Remote Similarity	NPD6118	Approved
0.6436	Remote Similarity	NPD6114	Approved
0.6429	Remote Similarity	NPD6067	Discontinued
0.6422	Remote Similarity	NPD5693	Phase 1
0.6404	Remote Similarity	NPD4159	Approved
0.64	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4753	Phase 2
0.6387	Remote Similarity	NPD5249	Phase 3
0.6387	Remote Similarity	NPD5247	Approved
0.6387	Remote Similarity	NPD5248	Approved
0.6387	Remote Similarity	NPD5250	Approved
0.6387	Remote Similarity	NPD5251	Approved
0.6355	Remote Similarity	NPD7524	Approved
0.6337	Remote Similarity	NPD6116	Phase 1
0.6333	Remote Similarity	NPD5215	Approved
0.6333	Remote Similarity	NPD5217	Approved
0.6333	Remote Similarity	NPD5216	Approved
0.6321	Remote Similarity	NPD1696	Phase 3
0.6306	Remote Similarity	NPD5282	Discontinued
0.63	Remote Similarity	NPD3703	Phase 2
0.6286	Remote Similarity	NPD7154	Phase 3
0.6275	Remote Similarity	NPD3617	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