NPASS Compound

Structure

NPC476004 OpenBabel07101718222D 31 32 0 0 1 0 0 0 0 0999 V2000 5.0059 2.1259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7833 -1.8245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1954 0.3267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3257 -2.8664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5334 1.8360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3704 -2.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1367 1.7073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6799 -1.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1228 -1.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1818 0.8871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3400 0.8006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6799 1.1288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5547 -0.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6531 -0.0916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1818 -1.0703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3983 0.8701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6282 -2.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5291 0.4515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5291 -0.6347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3792 0.8871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3792 -1.0703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4704 1.8321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1228 1.1288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7265 -0.6347 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2297 -3.4768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3983 -1.0533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6733 2.3756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4071 2.0507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3396 2.2507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9807 -1.8245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 4 17 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 25 2 0 0 0 0 17 30 1 0 0 0 0 18 16 1 1 0 0 0 19 26 1 1 0 0 0 20 23 1 1 0 0 0 20 31 1 0 0 0 0 21 24 1 6 0 0 0 21 30 1 0 0 0 0 22 27 2 0 0 0 0 22 29 1 0 0 0 0 23 5 1 1 0 0 0 23 28 1 0 0 0 0 24 6 1 6 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.26
Volume:	457.533
LogP:	2.465
LogD:	1.594
LogS:	-4.117
# Rotatable Bonds:	6
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.395
Synthetic Accessibility Score:	5.797
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.678
MDCK Permeability:	3.975584695581347e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.113
20% Bioavailability (F20%):	0.869
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	88.49097442626953%
Volume Distribution (VD):	1.277
Pgp-substrate:	8.708025932312012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.429
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.312
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	3.885
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.387
AMES Toxicity:	0.168
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.954
Carcinogencity:	0.11
Eye Corrosion:	0.124
Eye Irritation:	0.669
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC476004

Natural Product ID:	NPC476004
*Common Name:**	Dendronpholide O
IUPAC Name:	ethyl 2-[(1S,2R,5R,7R,8E,11S,12R)-11-acetyloxy-2,7-dihydroxy-2,8,12-trimethyl-15-oxabicyclo[10.2.1]pentadec-8-en-5-yl]prop-2-enoate
Synonyms:	Dendronpholide O
Standard InCHIKey:	KCGXIUGFHXCXBV-ALVRTLGPSA-N
Standard InCHI:	InChI=1S/C24H38O7/c1-7-29-22(27)16(3)18-10-12-23(5,28)20-11-13-24(6,31-20)21(30-17(4)25)9-8-15(2)19(26)14-18/h8,18-21,26,28H,3,7,9-14H2,1-2,4-6H3/b15-8+/t18-,19-,20+,21+,23-,24-/m1/s1
SMILES:	CCOC(=O)C(=C)C1CCC(C2CCC(O2)(C(CC=C(C(C1)O)C)OC(=O)C)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521106
PubChem CID:	44568452
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33216	dendronephthya sp.	Species	Nephtheidae	Eukaryota	n.a.	chinese soft coral	n.a.	PMID[18563933]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[535799]

☑ 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 NPC476004 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	191
0.1-0.2	1136
0.2-0.3	4223
0.3-0.4	7868
0.4-0.5	15030
0.5-0.6	7677
0.6-0.7	4780
0.7-0.8	1427
0.8-0.85	288
0.85-0.9	53
0.9-0.95	18
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474761
0.9651	High Similarity	NPC30515
0.9545	High Similarity	NPC36954
0.954	High Similarity	NPC475912
0.9535	High Similarity	NPC51004
0.9432	High Similarity	NPC474035
0.9432	High Similarity	NPC81386
0.9425	High Similarity	NPC184463
0.9419	High Similarity	NPC307411
0.9405	High Similarity	NPC137033
0.9326	High Similarity	NPC270013
0.9326	High Similarity	NPC14961
0.9318	High Similarity	NPC179746
0.9318	High Similarity	NPC476300
0.9318	High Similarity	NPC81419
0.9302	High Similarity	NPC153805
0.9302	High Similarity	NPC202672
0.9302	High Similarity	NPC474471
0.9302	High Similarity	NPC227379
0.9286	High Similarity	NPC474780
0.9222	High Similarity	NPC476315
0.9205	High Similarity	NPC12172
0.9205	High Similarity	NPC208886
0.9195	High Similarity	NPC474032
0.9186	High Similarity	NPC248602
0.9176	High Similarity	NPC21469
0.9167	High Similarity	NPC11620
0.9101	High Similarity	NPC212486
0.8977	High Similarity	NPC295312
0.8953	High Similarity	NPC329749
0.8864	High Similarity	NPC177629
0.8864	High Similarity	NPC58219
0.8864	High Similarity	NPC281516
0.8851	High Similarity	NPC475019
0.8851	High Similarity	NPC474949
0.8851	High Similarity	NPC164393
0.8837	High Similarity	NPC475963
0.8837	High Similarity	NPC151176
0.8837	High Similarity	NPC9868
0.8837	High Similarity	NPC3464
0.8837	High Similarity	NPC243618
0.8837	High Similarity	NPC70424
0.8791	High Similarity	NPC303942
0.8791	High Similarity	NPC57405
0.8778	High Similarity	NPC473321
0.8764	High Similarity	NPC92974
0.875	High Similarity	NPC179659
0.875	High Similarity	NPC186148
0.875	High Similarity	NPC231889
0.8736	High Similarity	NPC47958
0.8736	High Similarity	NPC304509
0.8736	High Similarity	NPC149725
0.8723	High Similarity	NPC288876
0.8721	High Similarity	NPC250315
0.8681	High Similarity	NPC162205
0.8681	High Similarity	NPC273579
0.8681	High Similarity	NPC288240
0.8681	High Similarity	NPC295204
0.8667	High Similarity	NPC473448
0.8667	High Similarity	NPC473619
0.8667	High Similarity	NPC475748
0.8652	High Similarity	NPC473715
0.8646	High Similarity	NPC472755
0.8636	High Similarity	NPC474762
0.8636	High Similarity	NPC476015
0.8621	High Similarity	NPC474776
0.8617	High Similarity	NPC187268
0.8617	High Similarity	NPC473326
0.8617	High Similarity	NPC474213
0.8602	High Similarity	NPC473859
0.8602	High Similarity	NPC279621
0.8557	High Similarity	NPC100487
0.8539	High Similarity	NPC160138
0.8539	High Similarity	NPC474765
0.8523	High Similarity	NPC477018
0.8523	High Similarity	NPC100921
0.8511	High Similarity	NPC40812
0.8495	Intermediate Similarity	NPC107476
0.8495	Intermediate Similarity	NPC272050
0.8495	Intermediate Similarity	NPC475659
0.8495	Intermediate Similarity	NPC471142
0.8478	Intermediate Similarity	NPC228451
0.8478	Intermediate Similarity	NPC475838
0.8478	Intermediate Similarity	NPC125674
0.8469	Intermediate Similarity	NPC243998
0.8462	Intermediate Similarity	NPC475855
0.8454	Intermediate Similarity	NPC475945
0.8454	Intermediate Similarity	NPC475871
0.8438	Intermediate Similarity	NPC474742
0.8438	Intermediate Similarity	NPC472753
0.8438	Intermediate Similarity	NPC476270
0.8427	Intermediate Similarity	NPC112685
0.8427	Intermediate Similarity	NPC477010
0.8427	Intermediate Similarity	NPC122502
0.8427	Intermediate Similarity	NPC309211
0.8427	Intermediate Similarity	NPC284902
0.8421	Intermediate Similarity	NPC471144
0.8421	Intermediate Similarity	NPC83895
0.8421	Intermediate Similarity	NPC187761
0.8409	Intermediate Similarity	NPC72464
0.8404	Intermediate Similarity	NPC477921
0.8391	Intermediate Similarity	NPC474291
0.8387	Intermediate Similarity	NPC474247
0.8387	Intermediate Similarity	NPC71589
0.8372	Intermediate Similarity	NPC474981
0.8372	Intermediate Similarity	NPC233377
0.8352	Intermediate Similarity	NPC151770
0.8352	Intermediate Similarity	NPC477011
0.8352	Intermediate Similarity	NPC173926
0.8352	Intermediate Similarity	NPC474951
0.8352	Intermediate Similarity	NPC473564
0.8351	Intermediate Similarity	NPC149371
0.8351	Intermediate Similarity	NPC472754
0.8351	Intermediate Similarity	NPC474747
0.8351	Intermediate Similarity	NPC86077
0.8351	Intermediate Similarity	NPC324017
0.8351	Intermediate Similarity	NPC320019
0.8333	Intermediate Similarity	NPC470401
0.8333	Intermediate Similarity	NPC475703
0.8333	Intermediate Similarity	NPC154097
0.8333	Intermediate Similarity	NPC159750
0.8333	Intermediate Similarity	NPC475053
0.8333	Intermediate Similarity	NPC473649
0.8315	Intermediate Similarity	NPC197903
0.8315	Intermediate Similarity	NPC99395
0.8315	Intermediate Similarity	NPC255307
0.8298	Intermediate Similarity	NPC477922
0.8298	Intermediate Similarity	NPC304886
0.8295	Intermediate Similarity	NPC272814
0.8283	Intermediate Similarity	NPC223450
0.8283	Intermediate Similarity	NPC472749
0.8283	Intermediate Similarity	NPC472751
0.828	Intermediate Similarity	NPC476049
0.828	Intermediate Similarity	NPC469645
0.828	Intermediate Similarity	NPC469692
0.8265	Intermediate Similarity	NPC472747
0.8265	Intermediate Similarity	NPC472750
0.8261	Intermediate Similarity	NPC106510
0.8261	Intermediate Similarity	NPC144133
0.8261	Intermediate Similarity	NPC179394
0.8261	Intermediate Similarity	NPC313670
0.8261	Intermediate Similarity	NPC71533
0.8247	Intermediate Similarity	NPC128733
0.8247	Intermediate Similarity	NPC110443
0.8247	Intermediate Similarity	NPC15993
0.8247	Intermediate Similarity	NPC150923
0.8247	Intermediate Similarity	NPC473332
0.8247	Intermediate Similarity	NPC185141
0.8247	Intermediate Similarity	NPC133907
0.8247	Intermediate Similarity	NPC47880
0.8247	Intermediate Similarity	NPC46998
0.8242	Intermediate Similarity	NPC89001
0.8235	Intermediate Similarity	NPC320630
0.8235	Intermediate Similarity	NPC7563
0.8235	Intermediate Similarity	NPC116177
0.8229	Intermediate Similarity	NPC255592
0.8229	Intermediate Similarity	NPC308567
0.8229	Intermediate Similarity	NPC261377
0.8222	Intermediate Similarity	NPC62118
0.8222	Intermediate Similarity	NPC475581
0.8222	Intermediate Similarity	NPC114694
0.8222	Intermediate Similarity	NPC142117
0.8222	Intermediate Similarity	NPC232555
0.8222	Intermediate Similarity	NPC171174
0.8222	Intermediate Similarity	NPC107717
0.8222	Intermediate Similarity	NPC240695
0.8222	Intermediate Similarity	NPC475461
0.8222	Intermediate Similarity	NPC305475
0.8222	Intermediate Similarity	NPC231096
0.8211	Intermediate Similarity	NPC76862
0.8211	Intermediate Similarity	NPC158416
0.8211	Intermediate Similarity	NPC230800
0.8211	Intermediate Similarity	NPC39859
0.8211	Intermediate Similarity	NPC470883
0.8202	Intermediate Similarity	NPC472957
0.8202	Intermediate Similarity	NPC191476
0.8202	Intermediate Similarity	NPC472958
0.8202	Intermediate Similarity	NPC114979
0.8202	Intermediate Similarity	NPC156804
0.82	Intermediate Similarity	NPC477513
0.8191	Intermediate Similarity	NPC473330
0.8191	Intermediate Similarity	NPC190294
0.8191	Intermediate Similarity	NPC473316
0.8191	Intermediate Similarity	NPC121825
0.8191	Intermediate Similarity	NPC474338
0.8182	Intermediate Similarity	NPC203659
0.8182	Intermediate Similarity	NPC145914
0.8182	Intermediate Similarity	NPC11332
0.8182	Intermediate Similarity	NPC131002
0.8182	Intermediate Similarity	NPC473780
0.8182	Intermediate Similarity	NPC65930
0.8182	Intermediate Similarity	NPC94875
0.8182	Intermediate Similarity	NPC73310
0.8182	Intermediate Similarity	NPC473712
0.8182	Intermediate Similarity	NPC474741
0.8182	Intermediate Similarity	NPC329829
0.8182	Intermediate Similarity	NPC473529
0.8182	Intermediate Similarity	NPC472748
0.8182	Intermediate Similarity	NPC475159
0.8182	Intermediate Similarity	NPC180363

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 NPC476004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1679
0.2-0.3	3580
0.3-0.4	2393
0.4-0.5	846
0.5-0.6	349
0.6-0.7	102
0.7-0.8	24
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
0.8261	Intermediate Similarity	NPD6698	Approved
0.8261	Intermediate Similarity	NPD46	Approved
0.8172	Intermediate Similarity	NPD7983	Approved
0.8111	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD7838	Discovery
0.7843	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD6371	Approved
0.7547	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5778	Approved
0.7526	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7154	Phase 3
0.7429	Intermediate Similarity	NPD6686	Approved
0.7374	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5344	Discontinued
0.7327	Intermediate Similarity	NPD4225	Approved
0.732	Intermediate Similarity	NPD5785	Approved
0.7312	Intermediate Similarity	NPD5362	Discontinued
0.7263	Intermediate Similarity	NPD5786	Approved
0.7216	Intermediate Similarity	NPD1695	Approved
0.7188	Intermediate Similarity	NPD4251	Approved
0.7188	Intermediate Similarity	NPD4250	Approved
0.7158	Intermediate Similarity	NPD5363	Approved
0.7156	Intermediate Similarity	NPD6053	Discontinued
0.7129	Intermediate Similarity	NPD7839	Suspended
0.7105	Intermediate Similarity	NPD8513	Phase 3
0.7105	Intermediate Similarity	NPD8517	Approved
0.7105	Intermediate Similarity	NPD8516	Approved
0.7105	Intermediate Similarity	NPD8515	Approved
0.7087	Intermediate Similarity	NPD7640	Approved
0.7087	Intermediate Similarity	NPD7639	Approved
0.7083	Intermediate Similarity	NPD4249	Approved
0.7021	Intermediate Similarity	NPD6435	Approved
0.7021	Intermediate Similarity	NPD4269	Approved
0.7021	Intermediate Similarity	NPD4270	Approved
0.699	Remote Similarity	NPD7638	Approved
0.6989	Remote Similarity	NPD4819	Approved
0.6989	Remote Similarity	NPD4821	Approved
0.6989	Remote Similarity	NPD4820	Approved
0.6989	Remote Similarity	NPD4822	Approved
0.6989	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6648	Approved
0.6915	Remote Similarity	NPD5369	Approved
0.6903	Remote Similarity	NPD7115	Discovery
0.6869	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6101	Approved
0.6842	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4252	Approved
0.6809	Remote Similarity	NPD5368	Approved
0.6807	Remote Similarity	NPD8074	Phase 3
0.6804	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4271	Approved
0.6774	Remote Similarity	NPD4268	Approved
0.6771	Remote Similarity	NPD5331	Approved
0.6771	Remote Similarity	NPD6110	Phase 1
0.6771	Remote Similarity	NPD5332	Approved
0.6737	Remote Similarity	NPD4790	Discontinued
0.6733	Remote Similarity	NPD6411	Approved
0.6727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7507	Approved
0.6637	Remote Similarity	NPD4632	Approved
0.6633	Remote Similarity	NPD1694	Approved
0.6602	Remote Similarity	NPD5282	Discontinued
0.6569	Remote Similarity	NPD7637	Suspended
0.6557	Remote Similarity	NPD7319	Approved
0.6555	Remote Similarity	NPD7642	Approved
0.6555	Remote Similarity	NPD7830	Approved
0.6555	Remote Similarity	NPD7829	Approved
0.6552	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7524	Approved
0.6486	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7632	Discontinued
0.6477	Remote Similarity	NPD7331	Phase 2
0.6457	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8039	Approved
0.6446	Remote Similarity	NPD8273	Phase 1
0.6446	Remote Similarity	NPD8451	Approved
0.6441	Remote Similarity	NPD6319	Approved
0.6437	Remote Similarity	NPD3197	Phase 1
0.641	Remote Similarity	NPD7641	Discontinued
0.6404	Remote Similarity	NPD8297	Approved
0.64	Remote Similarity	NPD6422	Discontinued
0.6396	Remote Similarity	NPD6412	Phase 2
0.6393	Remote Similarity	NPD8448	Approved
0.6387	Remote Similarity	NPD8444	Approved
0.6373	Remote Similarity	NPD5370	Suspended
0.6372	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7492	Approved
0.6364	Remote Similarity	NPD7341	Phase 2
0.6364	Remote Similarity	NPD8340	Approved
0.6364	Remote Similarity	NPD8299	Approved
0.6364	Remote Similarity	NPD8341	Approved
0.6364	Remote Similarity	NPD8342	Approved
0.6346	Remote Similarity	NPD6399	Phase 3
0.6339	Remote Similarity	NPD6881	Approved
0.6339	Remote Similarity	NPD6899	Approved
0.6327	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5209	Approved
0.6325	Remote Similarity	NPD6009	Approved
0.6321	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7260	Phase 2
0.6316	Remote Similarity	NPD4756	Discovery
0.6316	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6616	Approved
0.6306	Remote Similarity	NPD7128	Approved
0.6306	Remote Similarity	NPD6402	Approved
0.6306	Remote Similarity	NPD6675	Approved
0.6306	Remote Similarity	NPD6008	Approved
0.6306	Remote Similarity	NPD5739	Approved
0.6303	Remote Similarity	NPD6054	Approved
0.6281	Remote Similarity	NPD7604	Phase 2
0.6263	Remote Similarity	NPD6695	Phase 3
0.6262	Remote Similarity	NPD6083	Phase 2
0.6262	Remote Similarity	NPD6084	Phase 2
0.626	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD7909	Approved
0.624	Remote Similarity	NPD8390	Approved
0.624	Remote Similarity	NPD8392	Approved
0.624	Remote Similarity	NPD8391	Approved
0.6228	Remote Similarity	NPD7102	Approved
0.6228	Remote Similarity	NPD7290	Approved
0.6228	Remote Similarity	NPD6883	Approved
0.6228	Remote Similarity	NPD6421	Discontinued
0.621	Remote Similarity	NPD7736	Approved
0.6207	Remote Similarity	NPD8133	Approved
0.62	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6370	Approved
0.6195	Remote Similarity	NPD6011	Approved
0.6195	Remote Similarity	NPD7320	Approved
0.6186	Remote Similarity	NPD7500	Approved
0.6186	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6336	Discontinued
0.6174	Remote Similarity	NPD6650	Approved
0.6174	Remote Similarity	NPD6649	Approved
0.6174	Remote Similarity	NPD6869	Approved
0.6174	Remote Similarity	NPD6847	Approved
0.6174	Remote Similarity	NPD8130	Phase 1
0.6174	Remote Similarity	NPD6617	Approved
0.6167	Remote Similarity	NPD6059	Approved
0.6142	Remote Similarity	NPD6845	Suspended
0.614	Remote Similarity	NPD6014	Approved
0.614	Remote Similarity	NPD6373	Approved
0.614	Remote Similarity	NPD6013	Approved
0.614	Remote Similarity	NPD6372	Approved
0.614	Remote Similarity	NPD6012	Approved
0.6134	Remote Similarity	NPD7327	Approved
0.6134	Remote Similarity	NPD7328	Approved
0.6132	Remote Similarity	NPD7748	Approved
0.6129	Remote Similarity	NPD8293	Discontinued
0.6121	Remote Similarity	NPD6882	Approved
0.6116	Remote Similarity	NPD8033	Approved
0.6116	Remote Similarity	NPD6015	Approved
0.6116	Remote Similarity	NPD6016	Approved
0.6116	Remote Similarity	NPD7503	Approved
0.6106	Remote Similarity	NPD5701	Approved
0.6106	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6079	Approved
0.6095	Remote Similarity	NPD7515	Phase 2
0.6092	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7516	Approved
0.6078	Remote Similarity	NPD7146	Approved
0.6078	Remote Similarity	NPD7521	Approved
0.6078	Remote Similarity	NPD5330	Approved
0.6078	Remote Similarity	NPD6409	Approved
0.6078	Remote Similarity	NPD6684	Approved
0.6078	Remote Similarity	NPD7334	Approved
0.6075	Remote Similarity	NPD5695	Phase 3
0.6066	Remote Similarity	NPD5988	Approved
0.6066	Remote Similarity	NPD8080	Discontinued
0.6058	Remote Similarity	NPD5328	Approved
0.604	Remote Similarity	NPD4786	Approved
0.6036	Remote Similarity	NPD5211	Phase 2
0.6034	Remote Similarity	NPD2204	Approved
0.6034	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD8377	Approved
0.6033	Remote Similarity	NPD8294	Approved
0.6019	Remote Similarity	NPD7750	Discontinued
0.6016	Remote Similarity	NPD8328	Phase 3
0.6	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3667	Approved
0.5984	Remote Similarity	NPD8296	Approved
0.5984	Remote Similarity	NPD8380	Approved
0.5984	Remote Similarity	NPD8379	Approved
0.5984	Remote Similarity	NPD8378	Approved
0.5984	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD8335	Approved
0.5982	Remote Similarity	NPD6647	Phase 2
0.5963	Remote Similarity	NPD7902	Approved
0.5962	Remote Similarity	NPD6903	Approved
0.5962	Remote Similarity	NPD5737	Approved
0.5962	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6672	Approved
0.596	Remote Similarity	NPD6930	Phase 2
0.596	Remote Similarity	NPD6931	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