NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	348.19
Volume:	362.212
LogP:	3.498
LogD:	3.03
LogS:	-3.421
# Rotatable Bonds:	4
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.698
Synthetic Accessibility Score:	4.449
Fsp3:	0.65
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:	-5.806
MDCK Permeability:	8.526323654223233e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.084
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	93.19105529785156%
Volume Distribution (VD):	0.441
Pgp-substrate:	6.136075019836426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.32
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.2
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	2.102
Half-life (T1/2):	0.837

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.562
Maximum Recommended Daily Dose:	0.853
Skin Sensitization:	0.162
Carcinogencity:	0.69
Eye Corrosion:	0.067
Eye Irritation:	0.507
Respiratory Toxicity:	0.887

Download Data

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

Natural Product: NPC477782

Natural Product ID:	NPC477782
*Common Name:**	16-Hydroxy-8(17),13-labdadien-15,16-olid-19-oic acid
IUPAC Name:	(1S,4aR,5S,8aR)-5-[2-(2-hydroxy-5-oxo-2H-furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	GZTUAPFQPZVTGA-LTWMUGOISA-N
Standard InCHI:	InChI=1S/C20H28O5/c1-12-5-8-15-19(2,9-4-10-20(15,3)18(23)24)14(12)7-6-13-11-16(21)25-17(13)22/h11,14-15,17,22H,1,4-10H2,2-3H3,(H,23,24)/t14-,15+,17?,19+,20-/m0/s1
SMILES:	C[C@]12CCC[C@]([C@@H]1CCC(=C)[C@@H]2CCC3=CC(=O)OC3O)(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	14287153
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	Leaves and branches	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	leaves	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28256	Platycladus orientalis	Species	Cupressaceae	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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	84100	nM	PMID[15104493]

☑ 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 NPC477782 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	182
0.1-0.2	1043
0.2-0.3	4227
0.3-0.4	10446
0.4-0.5	12291
0.5-0.6	6786
0.6-0.7	6145
0.7-0.8	1387
0.8-0.85	132
0.85-0.9	44
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC477783
0.9647	High Similarity	NPC251528
0.9333	High Similarity	NPC475709
0.9176	High Similarity	NPC86316
0.9176	High Similarity	NPC106416
0.9176	High Similarity	NPC65661
0.913	High Similarity	NPC477720
0.908	High Similarity	NPC472810
0.908	High Similarity	NPC472809
0.907	High Similarity	NPC474062
0.9011	High Similarity	NPC470801
0.8977	High Similarity	NPC174342
0.8953	High Similarity	NPC42586
0.8953	High Similarity	NPC473251
0.8889	High Similarity	NPC472303
0.8876	High Similarity	NPC232426
0.8876	High Similarity	NPC281942
0.8876	High Similarity	NPC51486
0.8824	High Similarity	NPC200513
0.8791	High Similarity	NPC474554
0.8778	High Similarity	NPC289479
0.8778	High Similarity	NPC141831
0.8778	High Similarity	NPC177037
0.8778	High Similarity	NPC472811
0.8778	High Similarity	NPC472814
0.8764	High Similarity	NPC5509
0.8764	High Similarity	NPC470734
0.8723	High Similarity	NPC476767
0.8706	High Similarity	NPC40228
0.8706	High Similarity	NPC14203
0.8706	High Similarity	NPC229584
0.8681	High Similarity	NPC166346
0.8681	High Similarity	NPC472812
0.8681	High Similarity	NPC139692
0.8632	High Similarity	NPC63249
0.8621	High Similarity	NPC71626
0.8602	High Similarity	NPC17578
0.8602	High Similarity	NPC134072
0.8602	High Similarity	NPC242848
0.8602	High Similarity	NPC234993
0.8602	High Similarity	NPC240673
0.8587	High Similarity	NPC470255
0.8587	High Similarity	NPC469697
0.8587	High Similarity	NPC474555
0.8587	High Similarity	NPC324078
0.8571	High Similarity	NPC477122
0.8571	High Similarity	NPC165904
0.8571	High Similarity	NPC179517
0.8542	High Similarity	NPC134077
0.8539	High Similarity	NPC312561
0.8539	High Similarity	NPC475678
0.8523	High Similarity	NPC474860
0.8523	High Similarity	NPC471300
0.8523	High Similarity	NPC30984
0.8506	High Similarity	NPC311070
0.8495	Intermediate Similarity	NPC209355
0.8495	Intermediate Similarity	NPC472441
0.8485	Intermediate Similarity	NPC476765
0.8478	Intermediate Similarity	NPC115021
0.8478	Intermediate Similarity	NPC242069
0.8452	Intermediate Similarity	NPC61952
0.8444	Intermediate Similarity	NPC474629
0.8438	Intermediate Similarity	NPC471075
0.8409	Intermediate Similarity	NPC471302
0.8404	Intermediate Similarity	NPC325960
0.8404	Intermediate Similarity	NPC319692
0.8404	Intermediate Similarity	NPC162346
0.8391	Intermediate Similarity	NPC471296
0.8387	Intermediate Similarity	NPC104925
0.8387	Intermediate Similarity	NPC298973
0.8387	Intermediate Similarity	NPC475572
0.837	Intermediate Similarity	NPC65513
0.8353	Intermediate Similarity	NPC198240
0.8353	Intermediate Similarity	NPC239098
0.8352	Intermediate Similarity	NPC168131
0.8333	Intermediate Similarity	NPC472644
0.8317	Intermediate Similarity	NPC476766
0.8316	Intermediate Similarity	NPC477718
0.8316	Intermediate Similarity	NPC474343
0.8316	Intermediate Similarity	NPC208094
0.8316	Intermediate Similarity	NPC477719
0.8315	Intermediate Similarity	NPC189311
0.8315	Intermediate Similarity	NPC217394
0.83	Intermediate Similarity	NPC177524
0.83	Intermediate Similarity	NPC219900
0.83	Intermediate Similarity	NPC392
0.8298	Intermediate Similarity	NPC293052
0.8295	Intermediate Similarity	NPC472440
0.828	Intermediate Similarity	NPC469939
0.8247	Intermediate Similarity	NPC472643
0.8247	Intermediate Similarity	NPC303559
0.8229	Intermediate Similarity	NPC474440
0.8229	Intermediate Similarity	NPC473154
0.8222	Intermediate Similarity	NPC131813
0.8218	Intermediate Similarity	NPC476759
0.8202	Intermediate Similarity	NPC471301
0.8182	Intermediate Similarity	NPC471298
0.8172	Intermediate Similarity	NPC470113
0.8172	Intermediate Similarity	NPC329842
0.8163	Intermediate Similarity	NPC476769
0.8161	Intermediate Similarity	NPC10636
0.8152	Intermediate Similarity	NPC50488
0.8152	Intermediate Similarity	NPC474396
0.8144	Intermediate Similarity	NPC477716
0.8144	Intermediate Similarity	NPC477721
0.8144	Intermediate Similarity	NPC324841
0.8144	Intermediate Similarity	NPC117685
0.8125	Intermediate Similarity	NPC476253
0.8125	Intermediate Similarity	NPC257726
0.8125	Intermediate Similarity	NPC204054
0.8125	Intermediate Similarity	NPC253826
0.8111	Intermediate Similarity	NPC472442
0.8111	Intermediate Similarity	NPC329630
0.8105	Intermediate Similarity	NPC476488
0.8105	Intermediate Similarity	NPC476487
0.8105	Intermediate Similarity	NPC295347
0.809	Intermediate Similarity	NPC471297
0.809	Intermediate Similarity	NPC215893
0.8085	Intermediate Similarity	NPC470656
0.8085	Intermediate Similarity	NPC472871
0.8065	Intermediate Similarity	NPC182136
0.8065	Intermediate Similarity	NPC253186
0.8065	Intermediate Similarity	NPC78973
0.8061	Intermediate Similarity	NPC471412
0.8061	Intermediate Similarity	NPC477717
0.8043	Intermediate Similarity	NPC472378
0.8043	Intermediate Similarity	NPC472870
0.8043	Intermediate Similarity	NPC472302
0.8043	Intermediate Similarity	NPC104560
0.8043	Intermediate Similarity	NPC226863
0.8041	Intermediate Similarity	NPC316598
0.8023	Intermediate Similarity	NPC473756
0.8023	Intermediate Similarity	NPC316500
0.8022	Intermediate Similarity	NPC329692
0.8021	Intermediate Similarity	NPC29952
0.8021	Intermediate Similarity	NPC112654
0.8	Intermediate Similarity	NPC248758
0.8	Intermediate Similarity	NPC19849
0.8	Intermediate Similarity	NPC470800
0.8	Intermediate Similarity	NPC53685
0.8	Intermediate Similarity	NPC476415
0.8	Intermediate Similarity	NPC472864
0.8	Intermediate Similarity	NPC57117
0.8	Intermediate Similarity	NPC149869
0.798	Intermediate Similarity	NPC472815
0.798	Intermediate Similarity	NPC476081
0.7979	Intermediate Similarity	NPC476187
0.7979	Intermediate Similarity	NPC72845
0.7959	Intermediate Similarity	NPC471413
0.7959	Intermediate Similarity	NPC201406
0.7959	Intermediate Similarity	NPC474012
0.7959	Intermediate Similarity	NPC476299
0.7957	Intermediate Similarity	NPC66344
0.7941	Intermediate Similarity	NPC90946
0.7941	Intermediate Similarity	NPC325054
0.7941	Intermediate Similarity	NPC300614
0.7938	Intermediate Similarity	NPC476768
0.7938	Intermediate Similarity	NPC76266
0.7938	Intermediate Similarity	NPC53844
0.7931	Intermediate Similarity	NPC59436
0.7917	Intermediate Similarity	NPC183012
0.7912	Intermediate Similarity	NPC283733
0.7912	Intermediate Similarity	NPC52628
0.79	Intermediate Similarity	NPC112009
0.79	Intermediate Similarity	NPC471208
0.79	Intermediate Similarity	NPC120321
0.7895	Intermediate Similarity	NPC476416
0.7895	Intermediate Similarity	NPC267266
0.7895	Intermediate Similarity	NPC151722
0.7895	Intermediate Similarity	NPC205034
0.7895	Intermediate Similarity	NPC53555
0.7895	Intermediate Similarity	NPC472641
0.7895	Intermediate Similarity	NPC162615
0.7895	Intermediate Similarity	NPC472640
0.7895	Intermediate Similarity	NPC277721
0.7895	Intermediate Similarity	NPC152778
0.7889	Intermediate Similarity	NPC97913
0.7889	Intermediate Similarity	NPC42476
0.7889	Intermediate Similarity	NPC22611
0.7889	Intermediate Similarity	NPC193198
0.7872	Intermediate Similarity	NPC476369
0.7872	Intermediate Similarity	NPC472642
0.7872	Intermediate Similarity	NPC476437
0.7872	Intermediate Similarity	NPC232202
0.7872	Intermediate Similarity	NPC221111
0.7872	Intermediate Similarity	NPC472866
0.7872	Intermediate Similarity	NPC280149
0.7872	Intermediate Similarity	NPC8062
0.7872	Intermediate Similarity	NPC310479
0.7865	Intermediate Similarity	NPC90055
0.7864	Intermediate Similarity	NPC31522
0.7857	Intermediate Similarity	NPC108368
0.7857	Intermediate Similarity	NPC98868
0.7857	Intermediate Similarity	NPC57079
0.7857	Intermediate Similarity	NPC23364
0.7849	Intermediate Similarity	NPC196407
0.7843	Intermediate Similarity	NPC187435
0.7843	Intermediate Similarity	NPC67321
0.7841	Intermediate Similarity	NPC327674
0.7835	Intermediate Similarity	NPC202833

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 NPC477782 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1336
0.2-0.3	3665
0.3-0.4	2634
0.4-0.5	850
0.5-0.6	283
0.6-0.7	199
0.7-0.8	27
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD4752	Clinical (unspecified phase)
0.83	Intermediate Similarity	NPD6686	Approved
0.7802	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7639	Approved
0.7778	Intermediate Similarity	NPD7640	Approved
0.7677	Intermediate Similarity	NPD7638	Approved
0.7677	Intermediate Similarity	NPD4225	Approved
0.74	Intermediate Similarity	NPD6083	Phase 2
0.74	Intermediate Similarity	NPD6084	Phase 2
0.7292	Intermediate Similarity	NPD6672	Approved
0.7292	Intermediate Similarity	NPD5737	Approved
0.7273	Intermediate Similarity	NPD7748	Approved
0.7263	Intermediate Similarity	NPD6409	Approved
0.7263	Intermediate Similarity	NPD5330	Approved
0.7263	Intermediate Similarity	NPD6684	Approved
0.7263	Intermediate Similarity	NPD7334	Approved
0.7263	Intermediate Similarity	NPD7521	Approved
0.7263	Intermediate Similarity	NPD7146	Approved
0.7245	Intermediate Similarity	NPD7515	Phase 2
0.7245	Intermediate Similarity	NPD5693	Phase 1
0.7234	Intermediate Similarity	NPD3666	Approved
0.7234	Intermediate Similarity	NPD3133	Approved
0.7234	Intermediate Similarity	NPD3665	Phase 1
0.72	Intermediate Similarity	NPD5695	Phase 3
0.7172	Intermediate Similarity	NPD6399	Phase 3
0.717	Intermediate Similarity	NPD6412	Phase 2
0.7158	Intermediate Similarity	NPD1694	Approved
0.7157	Intermediate Similarity	NPD5696	Approved
0.7155	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD5785	Approved
0.7115	Intermediate Similarity	NPD7632	Discontinued
0.7113	Intermediate Similarity	NPD6903	Approved
0.7113	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3618	Phase 1
0.7083	Intermediate Similarity	NPD4623	Approved
0.7083	Intermediate Similarity	NPD4519	Discontinued
0.7059	Intermediate Similarity	NPD7902	Approved
0.7054	Intermediate Similarity	NPD7115	Discovery
0.7041	Intermediate Similarity	NPD4753	Phase 2
0.7037	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD8039	Approved
0.6989	Remote Similarity	NPD4695	Discontinued
0.6975	Remote Similarity	NPD7319	Approved
0.6957	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7128	Approved
0.6916	Remote Similarity	NPD5739	Approved
0.6916	Remote Similarity	NPD6675	Approved
0.6916	Remote Similarity	NPD6402	Approved
0.6907	Remote Similarity	NPD5279	Phase 3
0.69	Remote Similarity	NPD7637	Suspended
0.6875	Remote Similarity	NPD4786	Approved
0.6869	Remote Similarity	NPD6673	Approved
0.6869	Remote Similarity	NPD5328	Approved
0.6869	Remote Similarity	NPD6904	Approved
0.6869	Remote Similarity	NPD6080	Approved
0.6863	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5697	Approved
0.6852	Remote Similarity	NPD5701	Approved
0.6847	Remote Similarity	NPD6882	Approved
0.6842	Remote Similarity	NPD4223	Phase 3
0.6842	Remote Similarity	NPD7327	Approved
0.6842	Remote Similarity	NPD4221	Approved
0.6842	Remote Similarity	NPD7328	Approved
0.6832	Remote Similarity	NPD5779	Approved
0.6832	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6698	Approved
0.68	Remote Similarity	NPD46	Approved
0.6789	Remote Similarity	NPD6011	Approved
0.6789	Remote Similarity	NPD6881	Approved
0.6789	Remote Similarity	NPD7320	Approved
0.6789	Remote Similarity	NPD6899	Approved
0.6783	Remote Similarity	NPD7516	Approved
0.6771	Remote Similarity	NPD7154	Phase 3
0.6771	Remote Similarity	NPD5362	Discontinued
0.6768	Remote Similarity	NPD5208	Approved
0.6765	Remote Similarity	NPD7900	Approved
0.6765	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6411	Approved
0.6733	Remote Similarity	NPD6079	Approved
0.6733	Remote Similarity	NPD5281	Approved
0.6733	Remote Similarity	NPD5284	Approved
0.6727	Remote Similarity	NPD6014	Approved
0.6727	Remote Similarity	NPD6373	Approved
0.6727	Remote Similarity	NPD6372	Approved
0.6727	Remote Similarity	NPD6013	Approved
0.6727	Remote Similarity	NPD6012	Approved
0.6724	Remote Similarity	NPD8377	Approved
0.6724	Remote Similarity	NPD8294	Approved
0.6701	Remote Similarity	NPD4197	Approved
0.67	Remote Similarity	NPD6051	Approved
0.67	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5210	Approved
0.6699	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6637	Remote Similarity	NPD8133	Approved
0.6636	Remote Similarity	NPD5211	Phase 2
0.6635	Remote Similarity	NPD5221	Approved
0.6635	Remote Similarity	NPD5222	Approved
0.6635	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4697	Phase 3
0.6634	Remote Similarity	NPD5692	Phase 3
0.6633	Remote Similarity	NPD5329	Approved
0.6633	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5363	Approved
0.6607	Remote Similarity	NPD6847	Approved
0.6607	Remote Similarity	NPD6650	Approved
0.6607	Remote Similarity	NPD8130	Phase 1
0.6607	Remote Similarity	NPD6617	Approved
0.6607	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6869	Approved
0.6607	Remote Similarity	NPD6649	Approved
0.6604	Remote Similarity	NPD6404	Discontinued
0.6596	Remote Similarity	NPD3617	Approved
0.6571	Remote Similarity	NPD4755	Approved
0.6571	Remote Similarity	NPD5173	Approved
0.6569	Remote Similarity	NPD8034	Phase 2
0.6569	Remote Similarity	NPD8035	Phase 2
0.6569	Remote Similarity	NPD5694	Approved
0.6569	Remote Similarity	NPD6050	Approved
0.6566	Remote Similarity	NPD4138	Approved
0.6566	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6098	Approved
0.6566	Remote Similarity	NPD4688	Approved
0.6566	Remote Similarity	NPD4690	Approved
0.6566	Remote Similarity	NPD5205	Approved
0.6566	Remote Similarity	NPD4693	Phase 3
0.6566	Remote Similarity	NPD4689	Approved
0.6549	Remote Similarity	NPD6053	Discontinued
0.6549	Remote Similarity	NPD8297	Approved
0.6545	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6101	Approved
0.6531	Remote Similarity	NPD3668	Phase 3
0.6525	Remote Similarity	NPD7503	Approved
0.6518	Remote Similarity	NPD6371	Approved
0.6514	Remote Similarity	NPD5141	Approved
0.6509	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4269	Approved
0.6495	Remote Similarity	NPD4270	Approved
0.6495	Remote Similarity	NPD5209	Approved
0.6471	Remote Similarity	NPD5207	Approved
0.6466	Remote Similarity	NPD6009	Approved
0.6465	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5286	Approved
0.6449	Remote Similarity	NPD4700	Approved
0.6449	Remote Similarity	NPD4696	Approved
0.6449	Remote Similarity	NPD5285	Approved
0.6442	Remote Similarity	NPD6001	Approved
0.6429	Remote Similarity	NPD6695	Phase 3
0.6429	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4788	Approved
0.6417	Remote Similarity	NPD8328	Phase 3
0.64	Remote Similarity	NPD5280	Approved
0.64	Remote Similarity	NPD4694	Approved
0.64	Remote Similarity	NPD5690	Phase 2
0.64	Remote Similarity	NPD5786	Approved
0.6393	Remote Similarity	NPD8293	Discontinued
0.6389	Remote Similarity	NPD5223	Approved
0.6379	Remote Similarity	NPD6274	Approved
0.6379	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4632	Approved
0.6341	Remote Similarity	NPD7736	Approved
0.6333	Remote Similarity	NPD6370	Approved
0.633	Remote Similarity	NPD5224	Approved
0.633	Remote Similarity	NPD5225	Approved
0.633	Remote Similarity	NPD5226	Approved
0.633	Remote Similarity	NPD4633	Approved
0.6327	Remote Similarity	NPD6435	Approved
0.6325	Remote Similarity	NPD6317	Approved
0.6321	Remote Similarity	NPD7614	Phase 1
0.6321	Remote Similarity	NPD7839	Suspended
0.6316	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6008	Approved
0.6289	Remote Similarity	NPD4821	Approved
0.6289	Remote Similarity	NPD4252	Approved
0.6289	Remote Similarity	NPD4819	Approved
0.6289	Remote Similarity	NPD4822	Approved
0.6289	Remote Similarity	NPD4820	Approved
0.6281	Remote Similarity	NPD6067	Discontinued
0.6273	Remote Similarity	NPD4754	Approved
0.6273	Remote Similarity	NPD5174	Approved
0.6273	Remote Similarity	NPD5175	Approved
0.6271	Remote Similarity	NPD6335	Approved
0.6271	Remote Similarity	NPD6314	Approved
0.6271	Remote Similarity	NPD6313	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