NPASS Compound

Structure

NPC471219 OpenBabel07101718292D 23 25 0 0 1 0 0 0 0 0999 V2000 0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4597 0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9789 -0.3519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 1.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 -0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4265 2.1064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4982 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4977 1.8575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9560 0.4768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0561 1.5769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1064 1.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8127 0.0403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4982 0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 0.4808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9632 -0.9094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7628 -0.5853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4926 0.7202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 16 2 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 20 1 6 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 19 20 1 6 0 0 0 20 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	4.803
LogD:	4.198
LogS:	-4.603
# Rotatable Bonds:	3
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.785
Synthetic Accessibility Score:	4.618
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.661
MDCK Permeability:	1.6876838344614953e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.885
30% Bioavailability (F30%):	0.199

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	97.73921966552734%
Volume Distribution (VD):	2.43
Pgp-substrate:	3.8476858139038086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.133
CYP1A2-substrate:	0.592
CYP2C19-inhibitor:	0.571
CYP2C19-substrate:	0.627
CYP2C9-inhibitor:	0.503
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.213
CYP2D6-substrate:	0.321
CYP3A4-inhibitor:	0.571
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	10.408
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.397
Maximum Recommended Daily Dose:	0.725
Skin Sensitization:	0.09
Carcinogencity:	0.64
Eye Corrosion:	0.013
Eye Irritation:	0.535
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC471219

Natural Product ID:	NPC471219
*Common Name:**	(Rel-8R,9R,10S)-9-Hydroxylabda-5,13-Dien-15,16-Olide
IUPAC Name:	3-[2-[(1R,2R,8aS)-1-hydroxy-2,5,5,8a-tetramethyl-3,6,7,8-tetrahydro-2H-naphthalen-1-yl]ethyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	SMBFOAODHRAEJL-VOBQZIQPSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-14-6-7-16-18(2,3)9-5-10-19(16,4)20(14,22)11-8-15-12-17(21)23-13-15/h7,12,14,22H,5-6,8-11,13H2,1-4H3/t14-,19+,20-/m1/s1
SMILES:	O=C1OCC(=C1)CC[C@@]1(O)[C@H](C)CC=C2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2391693
PubChem CID:	71579372
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
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15621610]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28453270]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21373	Vitex trifolia	Species	Lamiaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT994	Cell Line	ZR-75-30	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[535778]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[535778]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[535778]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[535778]

☑ 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 NPC471219 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	165
0.1-0.2	1096
0.2-0.3	4373
0.3-0.4	10889
0.4-0.5	12636
0.5-0.6	6937
0.6-0.7	5366
0.7-0.8	1169
0.8-0.85	61
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8864	High Similarity	NPC7349
0.8764	High Similarity	NPC105490
0.8721	High Similarity	NPC471796
0.8667	High Similarity	NPC276110
0.8602	High Similarity	NPC472554
0.8588	High Similarity	NPC32223
0.8571	High Similarity	NPC29952
0.8571	High Similarity	NPC471218
0.8511	High Similarity	NPC472552
0.8511	High Similarity	NPC11956
0.8488	Intermediate Similarity	NPC471795
0.8488	Intermediate Similarity	NPC42586
0.8488	Intermediate Similarity	NPC473251
0.8471	Intermediate Similarity	NPC311070
0.8427	Intermediate Similarity	NPC221111
0.8427	Intermediate Similarity	NPC78973
0.8427	Intermediate Similarity	NPC280149
0.8421	Intermediate Similarity	NPC23584
0.8391	Intermediate Similarity	NPC131813
0.837	Intermediate Similarity	NPC165632
0.8333	Intermediate Similarity	NPC234335
0.8315	Intermediate Similarity	NPC470734
0.8315	Intermediate Similarity	NPC5509
0.8315	Intermediate Similarity	NPC261320
0.8315	Intermediate Similarity	NPC246028
0.8298	Intermediate Similarity	NPC471413
0.8298	Intermediate Similarity	NPC38855
0.8298	Intermediate Similarity	NPC324841
0.8298	Intermediate Similarity	NPC54705
0.8295	Intermediate Similarity	NPC312561
0.828	Intermediate Similarity	NPC51499
0.828	Intermediate Similarity	NPC205143
0.8276	Intermediate Similarity	NPC472442
0.8256	Intermediate Similarity	NPC472377
0.8256	Intermediate Similarity	NPC477124
0.8256	Intermediate Similarity	NPC476927
0.8256	Intermediate Similarity	NPC42476
0.8242	Intermediate Similarity	NPC475657
0.8229	Intermediate Similarity	NPC120009
0.8229	Intermediate Similarity	NPC45897
0.8222	Intermediate Similarity	NPC220216
0.8222	Intermediate Similarity	NPC182136
0.8222	Intermediate Similarity	NPC310479
0.8214	Intermediate Similarity	NPC242767
0.8214	Intermediate Similarity	NPC80471
0.8214	Intermediate Similarity	NPC5908
0.8214	Intermediate Similarity	NPC110373
0.8211	Intermediate Similarity	NPC268829
0.8211	Intermediate Similarity	NPC25177
0.8211	Intermediate Similarity	NPC222875
0.8211	Intermediate Similarity	NPC11974
0.8211	Intermediate Similarity	NPC471412
0.8211	Intermediate Similarity	NPC295110
0.8211	Intermediate Similarity	NPC247701
0.8202	Intermediate Similarity	NPC106332
0.8191	Intermediate Similarity	NPC325229
0.8191	Intermediate Similarity	NPC278673
0.8191	Intermediate Similarity	NPC275086
0.8161	Intermediate Similarity	NPC96055
0.8152	Intermediate Similarity	NPC298973
0.8152	Intermediate Similarity	NPC104925
0.8152	Intermediate Similarity	NPC140277
0.8152	Intermediate Similarity	NPC250075
0.8152	Intermediate Similarity	NPC469491
0.8152	Intermediate Similarity	NPC57117
0.814	Intermediate Similarity	NPC256112
0.8132	Intermediate Similarity	NPC472811
0.8132	Intermediate Similarity	NPC477574
0.8132	Intermediate Similarity	NPC124374
0.8132	Intermediate Similarity	NPC329842
0.8125	Intermediate Similarity	NPC109195
0.8125	Intermediate Similarity	NPC475038
0.8125	Intermediate Similarity	NPC476081
0.8125	Intermediate Similarity	NPC273005
0.8125	Intermediate Similarity	NPC469606
0.8125	Intermediate Similarity	NPC31058
0.8125	Intermediate Similarity	NPC162973
0.8118	Intermediate Similarity	NPC469802
0.8111	Intermediate Similarity	NPC474396
0.8111	Intermediate Similarity	NPC50488
0.8111	Intermediate Similarity	NPC170633
0.8105	Intermediate Similarity	NPC16601
0.8105	Intermediate Similarity	NPC476767
0.8095	Intermediate Similarity	NPC184737
0.809	Intermediate Similarity	NPC471779
0.8068	Intermediate Similarity	NPC86316
0.8068	Intermediate Similarity	NPC106416
0.8068	Intermediate Similarity	NPC253604
0.8068	Intermediate Similarity	NPC189311
0.8068	Intermediate Similarity	NPC65661
0.8068	Intermediate Similarity	NPC30984
0.8068	Intermediate Similarity	NPC474013
0.8065	Intermediate Similarity	NPC472441
0.8065	Intermediate Similarity	NPC295347
0.8061	Intermediate Similarity	NPC471206
0.8061	Intermediate Similarity	NPC220217
0.8061	Intermediate Similarity	NPC119855
0.8046	Intermediate Similarity	NPC49208
0.8046	Intermediate Similarity	NPC23748
0.8046	Intermediate Similarity	NPC193198
0.8046	Intermediate Similarity	NPC474809
0.8046	Intermediate Similarity	NPC472440
0.8043	Intermediate Similarity	NPC162615
0.8043	Intermediate Similarity	NPC205034
0.8043	Intermediate Similarity	NPC53555
0.8043	Intermediate Similarity	NPC99653
0.8043	Intermediate Similarity	NPC115021
0.8043	Intermediate Similarity	NPC152778
0.8043	Intermediate Similarity	NPC472812
0.8041	Intermediate Similarity	NPC189588
0.8041	Intermediate Similarity	NPC472821
0.8041	Intermediate Similarity	NPC97487
0.8041	Intermediate Similarity	NPC196471
0.8041	Intermediate Similarity	NPC160583
0.8041	Intermediate Similarity	NPC120321
0.8041	Intermediate Similarity	NPC10232
0.8041	Intermediate Similarity	NPC187302
0.8022	Intermediate Similarity	NPC158488
0.8022	Intermediate Similarity	NPC232426
0.8022	Intermediate Similarity	NPC38952
0.8022	Intermediate Similarity	NPC281942
0.8	Intermediate Similarity	NPC242448
0.8	Intermediate Similarity	NPC472810
0.8	Intermediate Similarity	NPC23364
0.8	Intermediate Similarity	NPC93411
0.8	Intermediate Similarity	NPC472378
0.8	Intermediate Similarity	NPC218107
0.8	Intermediate Similarity	NPC222303
0.8	Intermediate Similarity	NPC472809
0.7979	Intermediate Similarity	NPC134072
0.7979	Intermediate Similarity	NPC234993
0.7979	Intermediate Similarity	NPC209297
0.7979	Intermediate Similarity	NPC194132
0.7979	Intermediate Similarity	NPC475380
0.7978	Intermediate Similarity	NPC329692
0.7978	Intermediate Similarity	NPC102996
0.7976	Intermediate Similarity	NPC132542
0.7976	Intermediate Similarity	NPC283619
0.7976	Intermediate Similarity	NPC189206
0.7959	Intermediate Similarity	NPC200861
0.7957	Intermediate Similarity	NPC472360
0.7957	Intermediate Similarity	NPC472416
0.7957	Intermediate Similarity	NPC119562
0.7957	Intermediate Similarity	NPC474922
0.7957	Intermediate Similarity	NPC279410
0.7957	Intermediate Similarity	NPC470255
0.7957	Intermediate Similarity	NPC469697
0.7955	Intermediate Similarity	NPC306951
0.7955	Intermediate Similarity	NPC102048
0.7938	Intermediate Similarity	NPC472815
0.7938	Intermediate Similarity	NPC476769
0.7935	Intermediate Similarity	NPC473675
0.7935	Intermediate Similarity	NPC303697
0.7935	Intermediate Similarity	NPC141831
0.7935	Intermediate Similarity	NPC477122
0.7935	Intermediate Similarity	NPC78594
0.7935	Intermediate Similarity	NPC72845
0.7931	Intermediate Similarity	NPC2524
0.7917	Intermediate Similarity	NPC477721
0.7917	Intermediate Similarity	NPC251680
0.7917	Intermediate Similarity	NPC228251
0.7917	Intermediate Similarity	NPC477716
0.7917	Intermediate Similarity	NPC161527
0.7917	Intermediate Similarity	NPC219285
0.7917	Intermediate Similarity	NPC477968
0.7917	Intermediate Similarity	NPC20113
0.7917	Intermediate Similarity	NPC477972
0.7917	Intermediate Similarity	NPC474012
0.7917	Intermediate Similarity	NPC477971
0.7917	Intermediate Similarity	NPC476299
0.7912	Intermediate Similarity	NPC168131
0.7912	Intermediate Similarity	NPC174342
0.7912	Intermediate Similarity	NPC82876
0.7912	Intermediate Similarity	NPC473647
0.7912	Intermediate Similarity	NPC314727
0.7912	Intermediate Similarity	NPC470819
0.7907	Intermediate Similarity	NPC268827
0.7907	Intermediate Similarity	NPC10636
0.7907	Intermediate Similarity	NPC233332
0.79	Intermediate Similarity	NPC38948
0.79	Intermediate Similarity	NPC50124
0.7895	Intermediate Similarity	NPC231751
0.7895	Intermediate Similarity	NPC100912
0.7895	Intermediate Similarity	NPC98112
0.7895	Intermediate Similarity	NPC477719
0.7895	Intermediate Similarity	NPC475446
0.7895	Intermediate Similarity	NPC208094
0.7895	Intermediate Similarity	NPC473244
0.7895	Intermediate Similarity	NPC287668
0.7895	Intermediate Similarity	NPC477718
0.7895	Intermediate Similarity	NPC311241
0.7889	Intermediate Similarity	NPC166857
0.7889	Intermediate Similarity	NPC102640
0.7889	Intermediate Similarity	NPC131329
0.7889	Intermediate Similarity	NPC473891
0.7879	Intermediate Similarity	NPC172867
0.7879	Intermediate Similarity	NPC469607
0.7879	Intermediate Similarity	NPC186668
0.7879	Intermediate Similarity	NPC51719
0.7872	Intermediate Similarity	NPC37603

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 NPC471219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1408
0.2-0.3	3851
0.3-0.4	2507
0.4-0.5	802
0.5-0.6	277
0.6-0.7	153
0.7-0.8	8
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
0.8	Intermediate Similarity	NPD7638	Approved
0.7917	Intermediate Similarity	NPD7639	Approved
0.7917	Intermediate Similarity	NPD7640	Approved
0.7727	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD4225	Approved
0.7363	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6051	Approved
0.7308	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1694	Approved
0.7238	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7632	Discontinued
0.7212	Intermediate Similarity	NPD6686	Approved
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7129	Intermediate Similarity	NPD5344	Discontinued
0.7091	Intermediate Similarity	NPD7327	Approved
0.7091	Intermediate Similarity	NPD7328	Approved
0.7054	Intermediate Similarity	NPD8033	Approved
0.7041	Intermediate Similarity	NPD7748	Approved
0.703	Intermediate Similarity	NPD6648	Approved
0.7027	Intermediate Similarity	NPD7516	Approved
0.7021	Intermediate Similarity	NPD7521	Approved
0.7021	Intermediate Similarity	NPD7334	Approved
0.7021	Intermediate Similarity	NPD7146	Approved
0.7021	Intermediate Similarity	NPD6684	Approved
0.7021	Intermediate Similarity	NPD6409	Approved
0.7021	Intermediate Similarity	NPD5330	Approved
0.701	Intermediate Similarity	NPD5693	Phase 1
0.7	Intermediate Similarity	NPD4195	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.6964	Remote Similarity	NPD8377	Approved
0.6964	Remote Similarity	NPD8294	Approved
0.6952	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6053	Discontinued
0.6939	Remote Similarity	NPD6399	Phase 3
0.6931	Remote Similarity	NPD5696	Approved
0.6903	Remote Similarity	NPD8378	Approved
0.6903	Remote Similarity	NPD8380	Approved
0.6903	Remote Similarity	NPD7503	Approved
0.6903	Remote Similarity	NPD8379	Approved
0.6903	Remote Similarity	NPD8296	Approved
0.6903	Remote Similarity	NPD8335	Approved
0.6882	Remote Similarity	NPD6695	Phase 3
0.6875	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD6903	Approved
0.6867	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6008	Approved
0.6854	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7115	Discovery
0.6842	Remote Similarity	NPD4623	Approved
0.6842	Remote Similarity	NPD4519	Discontinued
0.6842	Remote Similarity	NPD3618	Phase 1
0.6837	Remote Similarity	NPD7637	Suspended
0.6837	Remote Similarity	NPD7515	Phase 2
0.6832	Remote Similarity	NPD7902	Approved
0.6809	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3666	Approved
0.6809	Remote Similarity	NPD3665	Phase 1
0.6809	Remote Similarity	NPD3133	Approved
0.6774	Remote Similarity	NPD3667	Approved
0.6774	Remote Similarity	NPD4223	Phase 3
0.6774	Remote Similarity	NPD4221	Approved
0.6771	Remote Similarity	NPD3573	Approved
0.6768	Remote Similarity	NPD5779	Approved
0.6768	Remote Similarity	NPD5778	Approved
0.6742	Remote Similarity	NPD7339	Approved
0.6742	Remote Similarity	NPD6942	Approved
0.6739	Remote Similarity	NPD6930	Phase 2
0.6739	Remote Similarity	NPD6931	Approved
0.6735	Remote Similarity	NPD6698	Approved
0.6735	Remote Similarity	NPD7838	Discovery
0.6735	Remote Similarity	NPD46	Approved
0.6701	Remote Similarity	NPD5208	Approved
0.6698	Remote Similarity	NPD6675	Approved
0.6698	Remote Similarity	NPD7128	Approved
0.6698	Remote Similarity	NPD6402	Approved
0.6698	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6634	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6080	Approved
0.6633	Remote Similarity	NPD4753	Phase 2
0.6633	Remote Similarity	NPD6904	Approved
0.6633	Remote Similarity	NPD6673	Approved
0.6633	Remote Similarity	NPD5328	Approved
0.6632	Remote Similarity	NPD4786	Approved
0.6632	Remote Similarity	NPD4197	Approved
0.663	Remote Similarity	NPD7645	Phase 2
0.663	Remote Similarity	NPD6929	Approved
0.6629	Remote Similarity	NPD6924	Approved
0.6629	Remote Similarity	NPD4784	Approved
0.6629	Remote Similarity	NPD6926	Approved
0.6629	Remote Similarity	NPD4785	Approved
0.6602	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4202	Approved
0.6598	Remote Similarity	NPD7524	Approved
0.6598	Remote Similarity	NPD7750	Discontinued
0.6591	Remote Similarity	NPD4243	Approved
0.6577	Remote Similarity	NPD4632	Approved
0.6574	Remote Similarity	NPD6011	Approved
0.6574	Remote Similarity	NPD7320	Approved
0.6574	Remote Similarity	NPD6899	Approved
0.6574	Remote Similarity	NPD6881	Approved
0.6566	Remote Similarity	NPD5207	Approved
0.6566	Remote Similarity	NPD5692	Phase 3
0.6562	Remote Similarity	NPD1696	Phase 3
0.6562	Remote Similarity	NPD5329	Approved
0.6559	Remote Similarity	NPD7332	Phase 2
0.6559	Remote Similarity	NPD4695	Discontinued
0.6559	Remote Similarity	NPD7525	Registered
0.6559	Remote Similarity	NPD7514	Phase 3
0.6556	Remote Similarity	NPD8039	Approved
0.6556	Remote Similarity	NPD8264	Approved
0.6548	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6001	Approved
0.6535	Remote Similarity	NPD7900	Approved
0.6514	Remote Similarity	NPD6012	Approved
0.6514	Remote Similarity	NPD6013	Approved
0.6514	Remote Similarity	NPD6373	Approved
0.6514	Remote Similarity	NPD6014	Approved
0.6514	Remote Similarity	NPD6372	Approved
0.65	Remote Similarity	NPD6079	Approved
0.65	Remote Similarity	NPD5694	Approved
0.65	Remote Similarity	NPD7319	Approved
0.65	Remote Similarity	NPD6411	Approved
0.65	Remote Similarity	NPD6050	Approved
0.6495	Remote Similarity	NPD5279	Phase 3
0.6495	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5280	Approved
0.6495	Remote Similarity	NPD5205	Approved
0.6495	Remote Similarity	NPD4693	Phase 3
0.6495	Remote Similarity	NPD4688	Approved
0.6495	Remote Similarity	NPD6098	Approved
0.6495	Remote Similarity	NPD4694	Approved
0.6495	Remote Similarity	NPD4138	Approved
0.6495	Remote Similarity	NPD4690	Approved
0.6495	Remote Similarity	NPD5690	Phase 2
0.6495	Remote Similarity	NPD4689	Approved
0.6484	Remote Similarity	NPD6933	Approved
0.6481	Remote Similarity	NPD6412	Phase 2
0.6465	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6883	Approved
0.6455	Remote Similarity	NPD6371	Approved
0.6455	Remote Similarity	NPD7290	Approved
0.6455	Remote Similarity	NPD7102	Approved
0.6413	Remote Similarity	NPD6925	Approved
0.6413	Remote Similarity	NPD5776	Phase 2
0.6413	Remote Similarity	NPD6932	Approved
0.6404	Remote Similarity	NPD6009	Approved
0.64	Remote Similarity	NPD5785	Approved
0.6396	Remote Similarity	NPD6869	Approved
0.6396	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD6649	Approved
0.6396	Remote Similarity	NPD6617	Approved
0.6396	Remote Similarity	NPD8130	Phase 1
0.6396	Remote Similarity	NPD6847	Approved
0.6396	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6893	Approved
0.6383	Remote Similarity	NPD7509	Discontinued
0.6383	Remote Similarity	NPD4748	Discontinued
0.6379	Remote Similarity	NPD6319	Approved
0.6374	Remote Similarity	NPD5275	Approved
0.6374	Remote Similarity	NPD4190	Phase 3
0.6373	Remote Similarity	NPD5282	Discontinued
0.6346	Remote Similarity	NPD4755	Approved
0.6344	Remote Similarity	NPD3617	Approved
0.6344	Remote Similarity	NPD7145	Approved
0.6344	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6882	Approved
0.6339	Remote Similarity	NPD8297	Approved
0.6337	Remote Similarity	NPD7087	Discontinued
0.633	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5983	Phase 2
0.6316	Remote Similarity	NPD6902	Approved
0.6316	Remote Similarity	NPD6898	Phase 1
0.6311	Remote Similarity	NPD4629	Approved
0.6311	Remote Similarity	NPD5210	Approved
0.6311	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4191	Approved
0.631	Remote Similarity	NPD4193	Approved
0.631	Remote Similarity	NPD4192	Approved
0.631	Remote Similarity	NPD4194	Approved
0.63	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.63	Remote Similarity	NPD1695	Approved
0.63	Remote Similarity	NPD6101	Approved
0.6289	Remote Similarity	NPD3668	Phase 3
0.6277	Remote Similarity	NPD6683	Phase 2
0.6262	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5209	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