NPASS Compound

Structure

NPC46320 OpenBabel07101718192D 21 23 0 0 1 0 0 0 0 0999 V2000 4.6137 0.8669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1482 -0.7078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2999 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2999 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -0.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -1.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -1.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 0.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4888 0.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3548 -1.0990 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3548 -0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -0.0990 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2209 -1.5990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8019 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 6 7 1 0 0 0 0 6 12 2 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 13 18 1 1 0 0 0 14 16 1 0 0 0 0 14 18 1 1 0 0 0 15 16 1 0 0 0 0 15 19 1 1 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.22
Volume:	317.949
LogP:	3.647
LogD:	3.508
LogS:	-2.822
# Rotatable Bonds:	0
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.695
Synthetic Accessibility Score:	4.272
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.605
MDCK Permeability:	2.1130426830495708e-05
Pgp-inhibitor:	0.234
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.28
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.649
Plasma Protein Binding (PPB):	68.37380981445312%
Volume Distribution (VD):	1.332
Pgp-substrate:	32.132469177246094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.431
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	9.202
Half-life (T1/2):	0.376

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.137
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.701
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.113
Carcinogencity:	0.331
Eye Corrosion:	0.006
Eye Irritation:	0.169
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC46320

Natural Product ID:	NPC46320
*Common Name:**	3Beta-Hydroxy-11,12-O-Isopropyldrimene
IUPAC Name:	(7aR,9S,11aS,11bR)-3,3,8,8,11a-pentamethyl-1,5,7,7a,9,10,11,11b-octahydrobenzo[g][2,4]benzodioxepin-9-ol
Synonyms:
Standard InCHIKey:	LQOFNPZEGRZRPE-YRBFXIGRSA-N
Standard InCHI:	InChI=1S/C18H30O3/c1-16(2)14-7-6-12-10-20-17(3,4)21-11-13(12)18(14,5)9-8-15(16)19/h6,13-15,19H,7-11H2,1-5H3/t13-,14-,15-,18+/m0/s1
SMILES:	O[C@H]1CC[C@]2([C@H](C1(C)C)CC=C1[C@@H]2COC(OC1)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172599
PubChem CID:	46912658
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002943] Dioxepanes [CHEMONTID:0002945] 1,3-dioxepanes

*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
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165144]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844878]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209522]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17279797]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20583752]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2847	Tissue	Thoracic aorta	Rattus norvegicus	Activity	=	32.1	%	PMID[504601]

☑ 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 NPC46320 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	196
0.1-0.2	1573
0.2-0.3	5036
0.3-0.4	13966
0.4-0.5	10864
0.5-0.6	7112
0.6-0.7	3385
0.7-0.8	556
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8721	High Similarity	NPC470819
0.8621	High Similarity	NPC470817
0.8554	High Similarity	NPC122945
0.8554	High Similarity	NPC109938
0.8444	Intermediate Similarity	NPC100892
0.8444	Intermediate Similarity	NPC477970
0.8415	Intermediate Similarity	NPC17550
0.8333	Intermediate Similarity	NPC189513
0.8333	Intermediate Similarity	NPC92801
0.8313	Intermediate Similarity	NPC206062
0.8256	Intermediate Similarity	NPC119001
0.8242	Intermediate Similarity	NPC135224
0.8242	Intermediate Similarity	NPC477969
0.8161	Intermediate Similarity	NPC173917
0.814	Intermediate Similarity	NPC319238
0.8118	Intermediate Similarity	NPC470049
0.8118	Intermediate Similarity	NPC155521
0.8118	Intermediate Similarity	NPC304285
0.809	Intermediate Similarity	NPC477917
0.8049	Intermediate Similarity	NPC265588
0.8046	Intermediate Similarity	NPC35933
0.8	Intermediate Similarity	NPC7505
0.8	Intermediate Similarity	NPC477792
0.8	Intermediate Similarity	NPC474683
0.8	Intermediate Similarity	NPC476646
0.8	Intermediate Similarity	NPC474752
0.8	Intermediate Similarity	NPC471432
0.8	Intermediate Similarity	NPC164022
0.8	Intermediate Similarity	NPC23954
0.8	Intermediate Similarity	NPC471433
0.8	Intermediate Similarity	NPC474731
0.8	Intermediate Similarity	NPC474759
0.8	Intermediate Similarity	NPC82986
0.7978	Intermediate Similarity	NPC471952
0.7976	Intermediate Similarity	NPC242767
0.7955	Intermediate Similarity	NPC255143
0.7952	Intermediate Similarity	NPC91594
0.7952	Intermediate Similarity	NPC283619
0.7931	Intermediate Similarity	NPC83702
0.7931	Intermediate Similarity	NPC470077
0.7927	Intermediate Similarity	NPC291503
0.7917	Intermediate Similarity	NPC238397
0.7917	Intermediate Similarity	NPC471363
0.7912	Intermediate Similarity	NPC472811
0.7907	Intermediate Similarity	NPC471408
0.7901	Intermediate Similarity	NPC220939
0.7901	Intermediate Similarity	NPC265485
0.7895	Intermediate Similarity	NPC161527
0.7895	Intermediate Similarity	NPC20113
0.7895	Intermediate Similarity	NPC477972
0.7895	Intermediate Similarity	NPC219285
0.7895	Intermediate Similarity	NPC477971
0.7895	Intermediate Similarity	NPC228251
0.7895	Intermediate Similarity	NPC477968
0.7889	Intermediate Similarity	NPC115607
0.7889	Intermediate Similarity	NPC246028
0.7889	Intermediate Similarity	NPC97103
0.7889	Intermediate Similarity	NPC261320
0.7889	Intermediate Similarity	NPC473647
0.7882	Intermediate Similarity	NPC96362
0.7882	Intermediate Similarity	NPC474592
0.7875	Intermediate Similarity	NPC34834
0.7872	Intermediate Similarity	NPC26307
0.7857	Intermediate Similarity	NPC476314
0.7848	Intermediate Similarity	NPC96484
0.7848	Intermediate Similarity	NPC208999
0.7841	Intermediate Similarity	NPC266511
0.7841	Intermediate Similarity	NPC477578
0.7841	Intermediate Similarity	NPC471795
0.7841	Intermediate Similarity	NPC290731
0.7841	Intermediate Similarity	NPC157257
0.7841	Intermediate Similarity	NPC274448
0.7835	Intermediate Similarity	NPC127933
0.7835	Intermediate Similarity	NPC475889
0.7835	Intermediate Similarity	NPC134270
0.7835	Intermediate Similarity	NPC7644
0.7835	Intermediate Similarity	NPC7613
0.7826	Intermediate Similarity	NPC472812
0.7805	Intermediate Similarity	NPC201048
0.7805	Intermediate Similarity	NPC476366
0.7805	Intermediate Similarity	NPC477138
0.7805	Intermediate Similarity	NPC243342
0.7802	Intermediate Similarity	NPC221111
0.7802	Intermediate Similarity	NPC78973
0.7802	Intermediate Similarity	NPC220216
0.7802	Intermediate Similarity	NPC280149
0.7791	Intermediate Similarity	NPC142163
0.7791	Intermediate Similarity	NPC25554
0.7789	Intermediate Similarity	NPC473154
0.7778	Intermediate Similarity	NPC167706
0.7766	Intermediate Similarity	NPC165632
0.7765	Intermediate Similarity	NPC233295
0.7755	Intermediate Similarity	NPC470321
0.7755	Intermediate Similarity	NPC264867
0.7755	Intermediate Similarity	NPC201880
0.7755	Intermediate Similarity	NPC473207
0.7755	Intermediate Similarity	NPC81567
0.7753	Intermediate Similarity	NPC131813
0.7753	Intermediate Similarity	NPC476217
0.7753	Intermediate Similarity	NPC473226
0.7753	Intermediate Similarity	NPC329692
0.7742	Intermediate Similarity	NPC472416
0.7742	Intermediate Similarity	NPC472360
0.7738	Intermediate Similarity	NPC470711
0.7738	Intermediate Similarity	NPC470758
0.7738	Intermediate Similarity	NPC471798
0.7738	Intermediate Similarity	NPC90979
0.7738	Intermediate Similarity	NPC472805
0.7717	Intermediate Similarity	NPC477574
0.7717	Intermediate Similarity	NPC233345
0.7717	Intermediate Similarity	NPC124374
0.7717	Intermediate Similarity	NPC186363
0.7717	Intermediate Similarity	NPC329842
0.7711	Intermediate Similarity	NPC477923
0.7711	Intermediate Similarity	NPC66566
0.7708	Intermediate Similarity	NPC64348
0.7701	Intermediate Similarity	NPC256112
0.7692	Intermediate Similarity	NPC20946
0.7692	Intermediate Similarity	NPC470734
0.7684	Intermediate Similarity	NPC98112
0.7683	Intermediate Similarity	NPC182717
0.7683	Intermediate Similarity	NPC471799
0.7677	Intermediate Similarity	NPC252296
0.7677	Intermediate Similarity	NPC172867
0.7674	Intermediate Similarity	NPC295131
0.7667	Intermediate Similarity	NPC476948
0.7667	Intermediate Similarity	NPC471779
0.7667	Intermediate Similarity	NPC189777
0.7667	Intermediate Similarity	NPC149224
0.7667	Intermediate Similarity	NPC131329
0.7667	Intermediate Similarity	NPC166857
0.766	Intermediate Similarity	NPC8774
0.766	Intermediate Similarity	NPC472441
0.766	Intermediate Similarity	NPC471372
0.766	Intermediate Similarity	NPC472189
0.766	Intermediate Similarity	NPC276110
0.766	Intermediate Similarity	NPC471362
0.766	Intermediate Similarity	NPC476894
0.7653	Intermediate Similarity	NPC471887
0.7653	Intermediate Similarity	NPC471886
0.7653	Intermediate Similarity	NPC473124
0.7653	Intermediate Similarity	NPC473123
0.7653	Intermediate Similarity	NPC471888
0.7653	Intermediate Similarity	NPC471450
0.7653	Intermediate Similarity	NPC471885
0.7647	Intermediate Similarity	NPC83351
0.7647	Intermediate Similarity	NPC22955
0.7647	Intermediate Similarity	NPC275910
0.7647	Intermediate Similarity	NPC99168
0.7647	Intermediate Similarity	NPC167891
0.7647	Intermediate Similarity	NPC300499
0.7647	Intermediate Similarity	NPC470396
0.7647	Intermediate Similarity	NPC474989
0.764	Intermediate Similarity	NPC473251
0.764	Intermediate Similarity	NPC42586
0.7634	Intermediate Similarity	NPC91654
0.7634	Intermediate Similarity	NPC67398
0.7634	Intermediate Similarity	NPC53555
0.7634	Intermediate Similarity	NPC99653
0.7634	Intermediate Similarity	NPC474792
0.7629	Intermediate Similarity	NPC176406
0.7625	Intermediate Similarity	NPC471238
0.7619	Intermediate Similarity	NPC106432
0.7619	Intermediate Similarity	NPC477925
0.7619	Intermediate Similarity	NPC470749
0.7619	Intermediate Similarity	NPC274079
0.7619	Intermediate Similarity	NPC253190
0.7614	Intermediate Similarity	NPC474789
0.7614	Intermediate Similarity	NPC470558
0.7614	Intermediate Similarity	NPC52108
0.7614	Intermediate Similarity	NPC23748
0.7609	Intermediate Similarity	NPC310479
0.7609	Intermediate Similarity	NPC77796
0.7609	Intermediate Similarity	NPC469403
0.7609	Intermediate Similarity	NPC295668
0.7609	Intermediate Similarity	NPC92885
0.7609	Intermediate Similarity	NPC476226
0.7604	Intermediate Similarity	NPC474440
0.76	Intermediate Similarity	NPC125423
0.76	Intermediate Similarity	NPC88013
0.76	Intermediate Similarity	NPC109376
0.76	Intermediate Similarity	NPC184512
0.7595	Intermediate Similarity	NPC202017
0.759	Intermediate Similarity	NPC91858
0.759	Intermediate Similarity	NPC471797
0.759	Intermediate Similarity	NPC306727
0.759	Intermediate Similarity	NPC100334
0.7586	Intermediate Similarity	NPC473420
0.7586	Intermediate Similarity	NPC159148
0.7586	Intermediate Similarity	NPC116202
0.7582	Intermediate Similarity	NPC472378
0.7579	Intermediate Similarity	NPC227583
0.7579	Intermediate Similarity	NPC88009
0.7579	Intermediate Similarity	NPC211810
0.7579	Intermediate Similarity	NPC8954
0.7579	Intermediate Similarity	NPC221801
0.7579	Intermediate Similarity	NPC94905
0.7579	Intermediate Similarity	NPC284194
0.7579	Intermediate Similarity	NPC12103
0.7579	Intermediate Similarity	NPC98457

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 NPC46320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1937
0.2-0.3	3877
0.3-0.4	2205
0.4-0.5	620
0.5-0.6	274
0.6-0.7	62
0.7-0.8	0
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
0.7558	Intermediate Similarity	NPD7645	Phase 2
0.7412	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7339	Approved
0.7294	Intermediate Similarity	NPD6942	Approved
0.7294	Intermediate Similarity	NPD8264	Approved
0.7273	Intermediate Similarity	NPD7525	Registered
0.7071	Intermediate Similarity	NPD4225	Approved
0.7071	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD3667	Approved
0.6915	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD368	Approved
0.6809	Remote Similarity	NPD3618	Phase 1
0.6782	Remote Similarity	NPD6926	Approved
0.6782	Remote Similarity	NPD6924	Approved
0.6774	Remote Similarity	NPD4786	Approved
0.6774	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6399	Phase 3
0.6703	Remote Similarity	NPD4748	Discontinued
0.6703	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6634	Remote Similarity	NPD7902	Approved
0.6633	Remote Similarity	NPD7515	Phase 2
0.6629	Remote Similarity	NPD6933	Approved
0.6607	Remote Similarity	NPD7328	Approved
0.6607	Remote Similarity	NPD7327	Approved
0.6602	Remote Similarity	NPD4159	Approved
0.6598	Remote Similarity	NPD6051	Approved
0.6598	Remote Similarity	NPD5328	Approved
0.6593	Remote Similarity	NPD6929	Approved
0.6579	Remote Similarity	NPD8033	Approved
0.6566	Remote Similarity	NPD4202	Approved
0.6552	Remote Similarity	NPD7152	Approved
0.6552	Remote Similarity	NPD7150	Approved
0.6552	Remote Similarity	NPD7151	Approved
0.6549	Remote Similarity	NPD7516	Approved
0.6542	Remote Similarity	NPD6686	Approved
0.6526	Remote Similarity	NPD1694	Approved
0.6522	Remote Similarity	NPD6931	Approved
0.6522	Remote Similarity	NPD6930	Phase 2
0.6512	Remote Similarity	NPD6923	Approved
0.6512	Remote Similarity	NPD6922	Approved
0.6491	Remote Similarity	NPD8294	Approved
0.6491	Remote Similarity	NPD8377	Approved
0.6484	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6079	Approved
0.6455	Remote Similarity	NPD6882	Approved
0.6442	Remote Similarity	NPD5344	Discontinued
0.6437	Remote Similarity	NPD7144	Approved
0.6437	Remote Similarity	NPD7143	Approved
0.6435	Remote Similarity	NPD8379	Approved
0.6435	Remote Similarity	NPD8378	Approved
0.6435	Remote Similarity	NPD7503	Approved
0.6435	Remote Similarity	NPD8296	Approved
0.6435	Remote Similarity	NPD8380	Approved
0.6435	Remote Similarity	NPD8335	Approved
0.6421	Remote Similarity	NPD3133	Approved
0.6421	Remote Similarity	NPD3666	Approved
0.6421	Remote Similarity	NPD3665	Phase 1
0.6404	Remote Similarity	NPD4785	Approved
0.6404	Remote Similarity	NPD4784	Approved
0.6392	Remote Similarity	NPD7750	Discontinued
0.6392	Remote Similarity	NPD7524	Approved
0.6383	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7632	Discontinued
0.6374	Remote Similarity	NPD5776	Phase 2
0.6374	Remote Similarity	NPD6925	Approved
0.6372	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD4243	Approved
0.6364	Remote Similarity	NPD3168	Discontinued
0.6355	Remote Similarity	NPD7128	Approved
0.6355	Remote Similarity	NPD6675	Approved
0.6355	Remote Similarity	NPD6402	Approved
0.6355	Remote Similarity	NPD5739	Approved
0.6344	Remote Similarity	NPD7514	Phase 3
0.6344	Remote Similarity	NPD7332	Phase 2
0.6337	Remote Similarity	NPD7900	Approved
0.6337	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD342	Phase 1
0.6311	Remote Similarity	NPD4755	Approved
0.6304	Remote Similarity	NPD7145	Approved
0.63	Remote Similarity	NPD6411	Approved
0.6296	Remote Similarity	NPD6412	Phase 2
0.6296	Remote Similarity	NPD5697	Approved
0.6296	Remote Similarity	NPD5701	Approved
0.6277	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD3668	Phase 3
0.6239	Remote Similarity	NPD6011	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD7320	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6238	Remote Similarity	NPD5779	Approved
0.6238	Remote Similarity	NPD5778	Approved
0.6226	Remote Similarity	NPD5211	Phase 2
0.6218	Remote Similarity	NPD7507	Approved
0.6214	Remote Similarity	NPD4697	Phase 3
0.6214	Remote Similarity	NPD5221	Approved
0.6214	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5222	Approved
0.6196	Remote Similarity	NPD6932	Approved
0.619	Remote Similarity	NPD4700	Approved
0.619	Remote Similarity	NPD4696	Approved
0.619	Remote Similarity	NPD6648	Approved
0.619	Remote Similarity	NPD5285	Approved
0.619	Remote Similarity	NPD5286	Approved
0.6186	Remote Similarity	NPD6893	Approved
0.6186	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6013	Approved
0.6182	Remote Similarity	NPD6014	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6182	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6012	Approved
0.6161	Remote Similarity	NPD6053	Discontinued
0.6154	Remote Similarity	NPD5173	Approved
0.6154	Remote Similarity	NPD5275	Approved
0.6154	Remote Similarity	NPD4190	Phase 3
0.6145	Remote Similarity	NPD1145	Discontinued
0.6139	Remote Similarity	NPD7087	Discontinued
0.6139	Remote Similarity	NPD7637	Suspended
0.6139	Remote Similarity	NPD8034	Phase 2
0.6139	Remote Similarity	NPD8035	Phase 2
0.6132	Remote Similarity	NPD5223	Approved
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6122	Remote Similarity	NPD6684	Approved
0.6122	Remote Similarity	NPD7521	Approved
0.6122	Remote Similarity	NPD5330	Approved
0.6122	Remote Similarity	NPD7146	Approved
0.6122	Remote Similarity	NPD7334	Approved
0.6122	Remote Similarity	NPD6409	Approved
0.6122	Remote Similarity	NPD5279	Phase 3
0.6111	Remote Similarity	NPD5141	Approved
0.6105	Remote Similarity	NPD6898	Phase 1
0.61	Remote Similarity	NPD6101	Approved
0.61	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5290	Discontinued
0.6095	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6009	Approved
0.6075	Remote Similarity	NPD4633	Approved
0.6075	Remote Similarity	NPD5225	Approved
0.6075	Remote Similarity	NPD5224	Approved
0.6075	Remote Similarity	NPD5226	Approved
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD6650	Approved
0.6071	Remote Similarity	NPD6649	Approved
0.6071	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6068	Remote Similarity	NPD6054	Approved
0.6068	Remote Similarity	NPD6059	Approved
0.6066	Remote Similarity	NPD7319	Approved
0.6064	Remote Similarity	NPD6683	Phase 2
0.6064	Remote Similarity	NPD4195	Approved
0.6061	Remote Similarity	NPD3573	Approved
0.6044	Remote Similarity	NPD1811	Approved
0.6044	Remote Similarity	NPD1810	Approved
0.602	Remote Similarity	NPD1696	Phase 3
0.602	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5174	Approved
0.6019	Remote Similarity	NPD5175	Approved
0.6019	Remote Similarity	NPD4754	Approved
0.6018	Remote Similarity	NPD8297	Approved
0.6017	Remote Similarity	NPD6015	Approved
0.6017	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD6928	Phase 2
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD4695	Discontinued
0.5978	Remote Similarity	NPD8039	Approved
0.5966	Remote Similarity	NPD5988	Approved
0.5966	Remote Similarity	NPD6370	Approved
0.5965	Remote Similarity	NPD8133	Approved
0.5962	Remote Similarity	NPD5695	Phase 3
0.5962	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4519	Discontinued
0.596	Remote Similarity	NPD4623	Approved
0.5948	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4753	Phase 2
0.593	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6067	Discontinued
0.5917	Remote Similarity	NPD8328	Phase 3
0.5909	Remote Similarity	NPD4767	Approved
0.5909	Remote Similarity	NPD4768	Approved
0.5909	Remote Similarity	NPD6008	Approved
0.5882	Remote Similarity	NPD8517	Approved
0.5882	Remote Similarity	NPD8515	Approved
0.5882	Remote Similarity	NPD8516	Approved
0.5882	Remote Similarity	NPD46	Approved
0.5882	Remote Similarity	NPD8513	Phase 3
0.5882	Remote Similarity	NPD6698	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