NPASS Compound

Structure

NPC227379 OpenBabel07101719252D 27 28 0 0 1 0 0 0 0 0999 V2000 1.9857 0.5523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2407 -2.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5985 -2.4801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8713 1.9419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7144 0.7749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4546 -1.1665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4546 -0.5631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2092 -1.7178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7608 0.3919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1869 0.5784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6862 -1.3447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6862 -0.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4132 -2.2449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2092 -0.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7608 -2.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0676 2.1415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9358 -1.9432 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1869 -2.3080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4132 0.5153 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4165 -0.8648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9358 0.2136 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3642 3.0544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2872 -3.2626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3362 -0.8648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7098 1.4282 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 14 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 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 12 22 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 11 1 1 0 0 0 19 24 1 6 0 0 0 20 22 1 1 0 0 0 20 26 1 0 0 0 0 21 25 2 0 0 0 0 21 27 1 0 0 0 0 22 5 1 1 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	402.724
LogP:	3.035
LogD:	2.383
LogS:	-4.193
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	5.578
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.72
MDCK Permeability:	3.31132578139659e-05
Pgp-inhibitor:	0.615
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.924
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	91.12742614746094%
Volume Distribution (VD):	1.135
Pgp-substrate:	7.252895832061768%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.109
CYP2C9-inhibitor:	0.345
CYP2C9-substrate:	0.365
CYP2D6-inhibitor:	0.119
CYP2D6-substrate:	0.342
CYP3A4-inhibitor:	0.514
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	3.763
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.728
Drug-inuced Liver Injury (DILI):	0.345
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.968
Carcinogencity:	0.045
Eye Corrosion:	0.377
Eye Irritation:	0.766
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC227379

Natural Product ID:	NPC227379
*Common Name:**	Dendronpholide B
IUPAC Name:	[(1R,3R,4E,7E,11S,12R)-3-hydroxy-4,8,12-trimethyl-15-methylidene-14-oxo-13-oxabicyclo[10.3.2]heptadeca-4,7-dien-11-yl] acetate
Synonyms:
Standard InCHIKey:	FYHZAJMWZNMCLN-XZIQCTLMSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-14-7-6-8-15(2)19(24)13-18-11-12-22(5,27-21(25)16(18)3)20(10-9-14)26-17(4)23/h7-8,18-20,24H,3,6,9-13H2,1-2,4-5H3/b14-7+,15-8+/t18-,19-,20+,22-/m1/s1
SMILES:	C/C/1=CC/C=C(C)/[C@@H](C[C@H]2CC[C@](C)([C@H](CC1)OC(=O)C)OC(=O)C2=C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517990
PubChem CID:	24970636
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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[468711]

☑ 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 NPC227379 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	220
0.1-0.2	1319
0.2-0.3	4846
0.3-0.4	9427
0.4-0.5	14931
0.5-0.6	7429
0.6-0.7	3613
0.7-0.8	825
0.8-0.85	69
0.85-0.9	12
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474471
0.9759	High Similarity	NPC153805
0.9639	High Similarity	NPC248602
0.9398	High Similarity	NPC137033
0.9302	High Similarity	NPC474761
0.9302	High Similarity	NPC476004
0.9294	High Similarity	NPC281516
0.9157	High Similarity	NPC11620
0.8977	High Similarity	NPC30515
0.8941	High Similarity	NPC329749
0.8889	High Similarity	NPC36954
0.8876	High Similarity	NPC475912
0.8864	High Similarity	NPC51004
0.8837	High Similarity	NPC474949
0.8837	High Similarity	NPC164393
0.8837	High Similarity	NPC475019
0.8824	High Similarity	NPC243618
0.8824	High Similarity	NPC474780
0.8824	High Similarity	NPC70424
0.8824	High Similarity	NPC9868
0.8791	High Similarity	NPC476315
0.8778	High Similarity	NPC81386
0.8778	High Similarity	NPC474035
0.8764	High Similarity	NPC184463
0.875	High Similarity	NPC474032
0.875	High Similarity	NPC307411
0.8721	High Similarity	NPC99395
0.8721	High Similarity	NPC197903
0.8681	High Similarity	NPC14961
0.8681	High Similarity	NPC270013
0.8667	High Similarity	NPC179746
0.8667	High Similarity	NPC476300
0.8667	High Similarity	NPC81419
0.8636	High Similarity	NPC202672
0.8621	High Similarity	NPC122502
0.8621	High Similarity	NPC476015
0.8621	High Similarity	NPC474762
0.8588	High Similarity	NPC474291
0.8571	High Similarity	NPC474981
0.8556	High Similarity	NPC12172
0.8556	High Similarity	NPC208886
0.8539	High Similarity	NPC295312
0.8506	High Similarity	NPC21469
0.8495	Intermediate Similarity	NPC40812
0.8462	Intermediate Similarity	NPC212486
0.8444	Intermediate Similarity	NPC473448
0.8404	Intermediate Similarity	NPC255592
0.8404	Intermediate Similarity	NPC83895
0.8404	Intermediate Similarity	NPC261377
0.8404	Intermediate Similarity	NPC308567
0.8404	Intermediate Similarity	NPC187761
0.8391	Intermediate Similarity	NPC3464
0.8391	Intermediate Similarity	NPC475963
0.8391	Intermediate Similarity	NPC474776
0.8391	Intermediate Similarity	NPC151176
0.8391	Intermediate Similarity	NPC72464
0.837	Intermediate Similarity	NPC57405
0.837	Intermediate Similarity	NPC303942
0.8353	Intermediate Similarity	NPC233377
0.8352	Intermediate Similarity	NPC329952
0.8333	Intermediate Similarity	NPC173926
0.8333	Intermediate Similarity	NPC474951
0.8316	Intermediate Similarity	NPC288876
0.8315	Intermediate Similarity	NPC231889
0.8315	Intermediate Similarity	NPC474765
0.8295	Intermediate Similarity	NPC149725
0.8295	Intermediate Similarity	NPC47958
0.8295	Intermediate Similarity	NPC304509
0.828	Intermediate Similarity	NPC272050
0.8276	Intermediate Similarity	NPC250315
0.8276	Intermediate Similarity	NPC257358
0.8276	Intermediate Similarity	NPC170377
0.8276	Intermediate Similarity	NPC474472
0.8261	Intermediate Similarity	NPC476049
0.8242	Intermediate Similarity	NPC475748
0.8222	Intermediate Similarity	NPC58219
0.8222	Intermediate Similarity	NPC177629
0.8191	Intermediate Similarity	NPC473859
0.8191	Intermediate Similarity	NPC279621
0.8182	Intermediate Similarity	NPC472958
0.8182	Intermediate Similarity	NPC472957
0.8172	Intermediate Similarity	NPC71589
0.8163	Intermediate Similarity	NPC100487
0.8152	Intermediate Similarity	NPC470379
0.8152	Intermediate Similarity	NPC473321
0.8152	Intermediate Similarity	NPC470373
0.8152	Intermediate Similarity	NPC475972
0.814	Intermediate Similarity	NPC103634
0.8132	Intermediate Similarity	NPC92974
0.8125	Intermediate Similarity	NPC475053
0.8111	Intermediate Similarity	NPC160138
0.8111	Intermediate Similarity	NPC179659
0.8111	Intermediate Similarity	NPC186148
0.809	Intermediate Similarity	NPC261380
0.809	Intermediate Similarity	NPC100921
0.809	Intermediate Similarity	NPC474547
0.809	Intermediate Similarity	NPC477018
0.8085	Intermediate Similarity	NPC471142
0.8085	Intermediate Similarity	NPC475659
0.8085	Intermediate Similarity	NPC304886
0.8081	Intermediate Similarity	NPC243998
0.8065	Intermediate Similarity	NPC273579
0.8065	Intermediate Similarity	NPC475838
0.8065	Intermediate Similarity	NPC162205
0.8065	Intermediate Similarity	NPC288240
0.8065	Intermediate Similarity	NPC295204
0.8065	Intermediate Similarity	NPC228451
0.8065	Intermediate Similarity	NPC125674
0.8061	Intermediate Similarity	NPC472755
0.8061	Intermediate Similarity	NPC475945
0.8061	Intermediate Similarity	NPC475871
0.8043	Intermediate Similarity	NPC475855
0.8043	Intermediate Similarity	NPC473619
0.8043	Intermediate Similarity	NPC313670
0.8041	Intermediate Similarity	NPC474742
0.8022	Intermediate Similarity	NPC473715
0.8021	Intermediate Similarity	NPC474213
0.8021	Intermediate Similarity	NPC187268
0.8021	Intermediate Similarity	NPC473326
0.8	Intermediate Similarity	NPC84360
0.8	Intermediate Similarity	NPC309211
0.8	Intermediate Similarity	NPC284902
0.8	Intermediate Similarity	NPC477010
0.7979	Intermediate Similarity	NPC474247
0.7959	Intermediate Similarity	NPC86077
0.7959	Intermediate Similarity	NPC474747
0.7952	Intermediate Similarity	NPC477085
0.7935	Intermediate Similarity	NPC212598
0.7935	Intermediate Similarity	NPC83423
0.7935	Intermediate Similarity	NPC151770
0.7935	Intermediate Similarity	NPC473564
0.7931	Intermediate Similarity	NPC474510
0.7912	Intermediate Similarity	NPC473649
0.7912	Intermediate Similarity	NPC159750
0.7912	Intermediate Similarity	NPC475703
0.7912	Intermediate Similarity	NPC470401
0.7912	Intermediate Similarity	NPC154097
0.7912	Intermediate Similarity	NPC477959
0.79	Intermediate Similarity	NPC223450
0.7895	Intermediate Similarity	NPC477922
0.7895	Intermediate Similarity	NPC107476
0.7889	Intermediate Similarity	NPC165162
0.7889	Intermediate Similarity	NPC471494
0.7889	Intermediate Similarity	NPC255307
0.7879	Intermediate Similarity	NPC110989
0.7872	Intermediate Similarity	NPC135776
0.7865	Intermediate Similarity	NPC272814
0.7857	Intermediate Similarity	NPC476270
0.7857	Intermediate Similarity	NPC471412
0.7857	Intermediate Similarity	NPC472753
0.7857	Intermediate Similarity	NPC150923
0.7849	Intermediate Similarity	NPC77337
0.7849	Intermediate Similarity	NPC144133
0.7849	Intermediate Similarity	NPC106510
0.7849	Intermediate Similarity	NPC71533
0.7849	Intermediate Similarity	NPC179394
0.7841	Intermediate Similarity	NPC325031
0.7835	Intermediate Similarity	NPC471144
0.7831	Intermediate Similarity	NPC477087
0.7831	Intermediate Similarity	NPC477086
0.7826	Intermediate Similarity	NPC89001
0.7816	Intermediate Similarity	NPC470244
0.7816	Intermediate Similarity	NPC469617
0.7816	Intermediate Similarity	NPC470239
0.7812	Intermediate Similarity	NPC477921
0.7812	Intermediate Similarity	NPC230800
0.7802	Intermediate Similarity	NPC112685
0.7802	Intermediate Similarity	NPC116575
0.7802	Intermediate Similarity	NPC311163
0.7802	Intermediate Similarity	NPC475461
0.7802	Intermediate Similarity	NPC469483
0.7802	Intermediate Similarity	NPC305475
0.7802	Intermediate Similarity	NPC470242
0.78	Intermediate Similarity	NPC203659
0.78	Intermediate Similarity	NPC474741
0.7791	Intermediate Similarity	NPC7563
0.7791	Intermediate Similarity	NPC116177
0.7791	Intermediate Similarity	NPC320630
0.7789	Intermediate Similarity	NPC65829
0.7789	Intermediate Similarity	NPC474338
0.7789	Intermediate Similarity	NPC470013
0.7789	Intermediate Similarity	NPC262133
0.7789	Intermediate Similarity	NPC473330
0.7789	Intermediate Similarity	NPC473316
0.7789	Intermediate Similarity	NPC477131
0.7789	Intermediate Similarity	NPC470010
0.7789	Intermediate Similarity	NPC323008
0.7789	Intermediate Similarity	NPC469632
0.7789	Intermediate Similarity	NPC198853
0.7778	Intermediate Similarity	NPC78673
0.7778	Intermediate Similarity	NPC149371
0.7778	Intermediate Similarity	NPC473596
0.7778	Intermediate Similarity	NPC186155
0.7778	Intermediate Similarity	NPC320019
0.7778	Intermediate Similarity	NPC191476
0.7778	Intermediate Similarity	NPC156804
0.7778	Intermediate Similarity	NPC324017
0.7778	Intermediate Similarity	NPC160517
0.7778	Intermediate Similarity	NPC114979
0.7778	Intermediate Similarity	NPC225353

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 NPC227379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	2000
0.2-0.3	3663
0.3-0.4	2140
0.4-0.5	781
0.5-0.6	287
0.6-0.7	49
0.7-0.8	12
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
0.8043	Intermediate Similarity	NPD6698	Approved
0.8043	Intermediate Similarity	NPD46	Approved
0.7957	Intermediate Similarity	NPD7983	Approved
0.7692	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7838	Discovery
0.7596	Intermediate Similarity	NPD6371	Approved
0.75	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD5778	Approved
0.7476	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6053	Discontinued
0.7283	Intermediate Similarity	NPD7154	Phase 3
0.7238	Intermediate Similarity	NPD6686	Approved
0.7172	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5344	Discontinued
0.7113	Intermediate Similarity	NPD5785	Approved
0.71	Intermediate Similarity	NPD7839	Suspended
0.7097	Intermediate Similarity	NPD5362	Discontinued
0.7059	Intermediate Similarity	NPD7639	Approved
0.7059	Intermediate Similarity	NPD7640	Approved
0.7053	Intermediate Similarity	NPD5786	Approved
0.7037	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD1695	Approved
0.6989	Remote Similarity	NPD6435	Approved
0.6961	Remote Similarity	NPD7638	Approved
0.6947	Remote Similarity	NPD5363	Approved
0.6923	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6648	Approved
0.6837	Remote Similarity	NPD6101	Approved
0.6837	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4269	Approved
0.6809	Remote Similarity	NPD4270	Approved
0.6804	Remote Similarity	NPD4251	Approved
0.6804	Remote Similarity	NPD4250	Approved
0.6796	Remote Similarity	NPD4225	Approved
0.6774	Remote Similarity	NPD4819	Approved
0.6774	Remote Similarity	NPD4821	Approved
0.6774	Remote Similarity	NPD4820	Approved
0.6774	Remote Similarity	NPD5368	Approved
0.6774	Remote Similarity	NPD4822	Approved
0.6774	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6110	Phase 1
0.6706	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5369	Approved
0.6701	Remote Similarity	NPD4249	Approved
0.67	Remote Similarity	NPD6411	Approved
0.6638	Remote Similarity	NPD8517	Approved
0.6638	Remote Similarity	NPD8516	Approved
0.6638	Remote Similarity	NPD8515	Approved
0.6638	Remote Similarity	NPD8513	Phase 3
0.6628	Remote Similarity	NPD7331	Phase 2
0.6596	Remote Similarity	NPD4252	Approved
0.6593	Remote Similarity	NPD8039	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6562	Remote Similarity	NPD5332	Approved
0.6562	Remote Similarity	NPD5331	Approved
0.6559	Remote Similarity	NPD4268	Approved
0.6559	Remote Similarity	NPD4271	Approved
0.6555	Remote Similarity	NPD7507	Approved
0.6545	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4790	Discontinued
0.6512	Remote Similarity	NPD7341	Phase 2
0.646	Remote Similarity	NPD4632	Approved
0.6455	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7632	Discontinued
0.6429	Remote Similarity	NPD1694	Approved
0.6417	Remote Similarity	NPD8273	Phase 1
0.6395	Remote Similarity	NPD3197	Phase 1
0.6393	Remote Similarity	NPD7319	Approved
0.6387	Remote Similarity	NPD7829	Approved
0.6387	Remote Similarity	NPD7642	Approved
0.6387	Remote Similarity	NPD7830	Approved
0.6373	Remote Similarity	NPD7637	Suspended
0.6372	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD8074	Phase 3
0.6364	Remote Similarity	NPD6422	Discontinued
0.6339	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6899	Approved
0.6306	Remote Similarity	NPD6881	Approved
0.6293	Remote Similarity	NPD6009	Approved
0.6289	Remote Similarity	NPD5209	Approved
0.6281	Remote Similarity	NPD8451	Approved
0.6277	Remote Similarity	NPD4756	Discovery
0.6273	Remote Similarity	NPD6402	Approved
0.6273	Remote Similarity	NPD7128	Approved
0.6273	Remote Similarity	NPD5739	Approved
0.6273	Remote Similarity	NPD6675	Approved
0.6271	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD7748	Approved
0.6239	Remote Similarity	NPD7641	Discontinued
0.6235	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8448	Approved
0.6226	Remote Similarity	NPD6083	Phase 2
0.6226	Remote Similarity	NPD6084	Phase 2
0.6218	Remote Similarity	NPD8444	Approved
0.6218	Remote Similarity	NPD5983	Phase 2
0.6216	Remote Similarity	NPD5697	Approved
0.6216	Remote Similarity	NPD6412	Phase 2
0.6214	Remote Similarity	NPD7515	Phase 2
0.6207	Remote Similarity	NPD7909	Approved
0.6198	Remote Similarity	NPD7492	Approved
0.6198	Remote Similarity	NPD8341	Approved
0.6198	Remote Similarity	NPD8342	Approved
0.6198	Remote Similarity	NPD8299	Approved
0.6198	Remote Similarity	NPD8340	Approved
0.6195	Remote Similarity	NPD6421	Discontinued
0.6195	Remote Similarity	NPD7290	Approved
0.6195	Remote Similarity	NPD6883	Approved
0.6195	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD5370	Suspended
0.6172	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.616	Remote Similarity	NPD7260	Phase 2
0.6154	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD7500	Approved
0.6148	Remote Similarity	NPD6616	Approved
0.6148	Remote Similarity	NPD6336	Discontinued
0.614	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD6869	Approved
0.614	Remote Similarity	NPD6617	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6649	Approved
0.6139	Remote Similarity	NPD7524	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6122	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6372	Approved
0.6106	Remote Similarity	NPD6012	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6106	Remote Similarity	NPD6014	Approved
0.6106	Remote Similarity	NPD6373	Approved
0.6098	Remote Similarity	NPD7078	Approved
0.6087	Remote Similarity	NPD6882	Approved
0.608	Remote Similarity	NPD8390	Approved
0.608	Remote Similarity	NPD8392	Approved
0.608	Remote Similarity	NPD8391	Approved
0.6075	Remote Similarity	NPD7902	Approved
0.6071	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5701	Approved
0.6061	Remote Similarity	NPD6695	Phase 3
0.6058	Remote Similarity	NPD6079	Approved
0.6058	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7736	Approved
0.604	Remote Similarity	NPD5330	Approved
0.604	Remote Similarity	NPD7334	Approved
0.604	Remote Similarity	NPD6409	Approved
0.604	Remote Similarity	NPD6684	Approved
0.604	Remote Similarity	NPD7521	Approved
0.604	Remote Similarity	NPD7146	Approved
0.6038	Remote Similarity	NPD5695	Phase 3
0.6034	Remote Similarity	NPD8133	Approved
0.6033	Remote Similarity	NPD6370	Approved
0.6019	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6059	Approved
0.5984	Remote Similarity	NPD8328	Phase 3
0.5982	Remote Similarity	NPD5048	Discontinued
0.5982	Remote Similarity	NPD6008	Approved
0.5981	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3573	Approved
0.5969	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8293	Discontinued
0.5966	Remote Similarity	NPD7328	Approved
0.5966	Remote Similarity	NPD7327	Approved
0.595	Remote Similarity	NPD6016	Approved
0.595	Remote Similarity	NPD6015	Approved
0.595	Remote Similarity	NPD7503	Approved
0.5946	Remote Similarity	NPD6647	Phase 2
0.5922	Remote Similarity	NPD6672	Approved
0.5922	Remote Similarity	NPD5737	Approved
0.5922	Remote Similarity	NPD6903	Approved
0.5922	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7516	Approved
0.5905	Remote Similarity	NPD5693	Phase 1
0.5904	Remote Similarity	NPD3195	Phase 2
0.5904	Remote Similarity	NPD3194	Approved
0.5904	Remote Similarity	NPD4266	Approved
0.5904	Remote Similarity	NPD3196	Approved
0.5902	Remote Similarity	NPD5988	Approved
0.5893	Remote Similarity	NPD5141	Approved
0.5882	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5696	Approved
0.5868	Remote Similarity	NPD8377	Approved
0.5868	Remote Similarity	NPD8294	Approved
0.5865	Remote Similarity	NPD6051	Approved
0.5859	Remote Similarity	NPD6845	Suspended
0.5842	Remote Similarity	NPD4786	Approved
0.5842	Remote Similarity	NPD3133	Approved
0.5842	Remote Similarity	NPD3666	Approved
0.5842	Remote Similarity	NPD3665	Phase 1

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