NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	254.634
LogP:	4.682
LogD:	3.992
LogS:	-3.858
# Rotatable Bonds:	0
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	3.924
Fsp3:	0.733
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:	-4.667
MDCK Permeability:	2.3896644052001648e-05
Pgp-inhibitor:	0.109
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.686

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	94.63188934326172%
Volume Distribution (VD):	2.317
Pgp-substrate:	4.937723159790039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.204
CYP1A2-substrate:	0.523
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.625
CYP2C9-inhibitor:	0.341
CYP2C9-substrate:	0.808
CYP2D6-inhibitor:	0.132
CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	15.171
Half-life (T1/2):	0.232

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.294
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.386
Skin Sensitization:	0.508
Carcinogencity:	0.914
Eye Corrosion:	0.038
Eye Irritation:	0.45
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC195424

Natural Product ID:	NPC195424
*Common Name:**	Drimenin
IUPAC Name:	(5aS,9aS,9bR)-6,6,9a-trimethyl-5,5a,7,8,9,9b-hexahydro-3H-benzo[g][2]benzofuran-1-one
Synonyms:	Drimenin
Standard InCHIKey:	BQNSBENKJCLJGN-ZOWXZIJZSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)11(14)6-5-10-9-17-13(16)12(10)15/h5,11-12H,4,6-9H2,1-3H3/t11-,12+,15-/m0/s1
SMILES:	O=C1OCC2=CC[C@@H]3[C@]([C@@H]12)(C)CCCC3(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457165
PubChem CID:	442202
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO27061	Drimys winteri	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29634269]
NPO33499	porella cordeana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350093]
NPO27061	Drimys winteri	Species	Winteraceae	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	3
Others	4

Activity Type	# Activity
Individual Protein	1
Organism	3
Protein Complex	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	IC50	=	13800.0	nM	PMID[557339]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	200.0	ug ml-1	PMID[557338]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	1000.0	ug ml-1	PMID[557338]
NPT409	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Homo sapiens	Inhibition	=	100.0	%	PMID[557339]
NPT409	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Homo sapiens	IC50	=	970.0	nM	PMID[557339]
NPT411	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Homo sapiens	IC50	=	1780.0	nM	PMID[557339]

☑ 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 NPC195424 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	162
0.1-0.2	1097
0.2-0.3	4906
0.3-0.4	14643
0.4-0.5	9014
0.5-0.6	6917
0.6-0.7	4724
0.7-0.8	1152
0.8-0.85	59
0.85-0.9	17
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.961	High Similarity	NPC22611
0.9231	High Similarity	NPC186276
0.92	High Similarity	NPC41017
0.9024	High Similarity	NPC477128
0.8987	High Similarity	NPC178676
0.8961	High Similarity	NPC35574
0.8916	High Similarity	NPC168131
0.8831	High Similarity	NPC316500
0.881	High Similarity	NPC469595
0.881	High Similarity	NPC212679
0.881	High Similarity	NPC220454
0.8795	High Similarity	NPC215831
0.8795	High Similarity	NPC226863
0.8706	High Similarity	NPC49420
0.8706	High Similarity	NPC65513
0.869	High Similarity	NPC73995
0.8659	High Similarity	NPC189311
0.8659	High Similarity	NPC110405
0.8642	High Similarity	NPC193198
0.8605	High Similarity	NPC166346
0.8605	High Similarity	NPC475657
0.8588	High Similarity	NPC152467
0.8519	High Similarity	NPC200513
0.8506	High Similarity	NPC250075
0.8506	High Similarity	NPC477129
0.8506	High Similarity	NPC477130
0.8488	Intermediate Similarity	NPC186363
0.8488	Intermediate Similarity	NPC233345
0.8434	Intermediate Similarity	NPC52628
0.8434	Intermediate Similarity	NPC177932
0.8415	Intermediate Similarity	NPC470948
0.8409	Intermediate Similarity	NPC183012
0.8395	Intermediate Similarity	NPC229584
0.8395	Intermediate Similarity	NPC14203
0.8395	Intermediate Similarity	NPC475665
0.8395	Intermediate Similarity	NPC38642
0.8395	Intermediate Similarity	NPC282293
0.8372	Intermediate Similarity	NPC469372
0.8354	Intermediate Similarity	NPC187568
0.8354	Intermediate Similarity	NPC41780
0.8333	Intermediate Similarity	NPC250981
0.8333	Intermediate Similarity	NPC220478
0.8333	Intermediate Similarity	NPC6979
0.8315	Intermediate Similarity	NPC112654
0.8313	Intermediate Similarity	NPC100391
0.8313	Intermediate Similarity	NPC30486
0.8293	Intermediate Similarity	NPC226988
0.8256	Intermediate Similarity	NPC5509
0.8256	Intermediate Similarity	NPC284561
0.825	Intermediate Similarity	NPC4827
0.8235	Intermediate Similarity	NPC171722
0.8235	Intermediate Similarity	NPC312561
0.8222	Intermediate Similarity	NPC257726
0.8222	Intermediate Similarity	NPC204054
0.8214	Intermediate Similarity	NPC106416
0.8214	Intermediate Similarity	NPC65661
0.8214	Intermediate Similarity	NPC470223
0.8214	Intermediate Similarity	NPC86316
0.8161	Intermediate Similarity	NPC158488
0.8161	Intermediate Similarity	NPC101651
0.8161	Intermediate Similarity	NPC15059
0.8161	Intermediate Similarity	NPC159748
0.8148	Intermediate Similarity	NPC327674
0.8148	Intermediate Similarity	NPC150646
0.814	Intermediate Similarity	NPC472302
0.814	Intermediate Similarity	NPC277771
0.814	Intermediate Similarity	NPC24816
0.8132	Intermediate Similarity	NPC23364
0.8118	Intermediate Similarity	NPC470050
0.8118	Intermediate Similarity	NPC470051
0.8118	Intermediate Similarity	NPC329692
0.8095	Intermediate Similarity	NPC139566
0.8095	Intermediate Similarity	NPC71626
0.809	Intermediate Similarity	NPC470697
0.8072	Intermediate Similarity	NPC268122
0.8046	Intermediate Similarity	NPC173042
0.8046	Intermediate Similarity	NPC174342
0.8025	Intermediate Similarity	NPC471220
0.8023	Intermediate Similarity	NPC167877
0.8	Intermediate Similarity	NPC235906
0.8	Intermediate Similarity	NPC147921
0.8	Intermediate Similarity	NPC899
0.8	Intermediate Similarity	NPC92489
0.8	Intermediate Similarity	NPC295347
0.7978	Intermediate Similarity	NPC115021
0.7978	Intermediate Similarity	NPC471571
0.7976	Intermediate Similarity	NPC470046
0.7976	Intermediate Similarity	NPC470047
0.7976	Intermediate Similarity	NPC118423
0.7976	Intermediate Similarity	NPC222358
0.7976	Intermediate Similarity	NPC194637
0.7975	Intermediate Similarity	NPC306928
0.7975	Intermediate Similarity	NPC166797
0.7957	Intermediate Similarity	NPC63249
0.7955	Intermediate Similarity	NPC281942
0.7955	Intermediate Similarity	NPC232426
0.7955	Intermediate Similarity	NPC76286
0.7955	Intermediate Similarity	NPC8062
0.7952	Intermediate Similarity	NPC474955
0.7952	Intermediate Similarity	NPC40228
0.7952	Intermediate Similarity	NPC327002
0.7949	Intermediate Similarity	NPC129665
0.7935	Intermediate Similarity	NPC216478
0.7931	Intermediate Similarity	NPC28227
0.7931	Intermediate Similarity	NPC474845
0.7927	Intermediate Similarity	NPC242767
0.7922	Intermediate Similarity	NPC199557
0.7912	Intermediate Similarity	NPC307164
0.7912	Intermediate Similarity	NPC311166
0.7907	Intermediate Similarity	NPC474062
0.7907	Intermediate Similarity	NPC118266
0.7907	Intermediate Similarity	NPC85698
0.7907	Intermediate Similarity	NPC264127
0.7907	Intermediate Similarity	NPC9231
0.7901	Intermediate Similarity	NPC472300
0.7901	Intermediate Similarity	NPC65603
0.7889	Intermediate Similarity	NPC38830
0.7882	Intermediate Similarity	NPC159635
0.7882	Intermediate Similarity	NPC475100
0.7882	Intermediate Similarity	NPC219011
0.7882	Intermediate Similarity	NPC312660
0.7882	Intermediate Similarity	NPC470011
0.7882	Intermediate Similarity	NPC149869
0.7875	Intermediate Similarity	NPC65650
0.7875	Intermediate Similarity	NPC228978
0.7875	Intermediate Similarity	NPC476795
0.7872	Intermediate Similarity	NPC134077
0.7872	Intermediate Similarity	NPC469606
0.7872	Intermediate Similarity	NPC273005
0.7872	Intermediate Similarity	NPC31058
0.7865	Intermediate Similarity	NPC303697
0.7865	Intermediate Similarity	NPC190442
0.7865	Intermediate Similarity	NPC141831
0.7857	Intermediate Similarity	NPC240302
0.7857	Intermediate Similarity	NPC471218
0.7848	Intermediate Similarity	NPC135703
0.7841	Intermediate Similarity	NPC50488
0.7841	Intermediate Similarity	NPC174765
0.7841	Intermediate Similarity	NPC471222
0.7841	Intermediate Similarity	NPC288699
0.7841	Intermediate Similarity	NPC251528
0.7841	Intermediate Similarity	NPC474396
0.7831	Intermediate Similarity	NPC233332
0.7826	Intermediate Similarity	NPC474343
0.7826	Intermediate Similarity	NPC76266
0.7826	Intermediate Similarity	NPC208094
0.7826	Intermediate Similarity	NPC10057
0.7816	Intermediate Similarity	NPC181103
0.7816	Intermediate Similarity	NPC305029
0.7816	Intermediate Similarity	NPC175293
0.7805	Intermediate Similarity	NPC239098
0.7805	Intermediate Similarity	NPC184737
0.7805	Intermediate Similarity	NPC321514
0.7802	Intermediate Similarity	NPC33473
0.7802	Intermediate Similarity	NPC473369
0.7792	Intermediate Similarity	NPC476945
0.7791	Intermediate Similarity	NPC323765
0.7791	Intermediate Similarity	NPC30984
0.7791	Intermediate Similarity	NPC329738
0.7791	Intermediate Similarity	NPC476678
0.7791	Intermediate Similarity	NPC470048
0.7789	Intermediate Similarity	NPC36688
0.7789	Intermediate Similarity	NPC254202
0.7778	Intermediate Similarity	NPC473223
0.7778	Intermediate Similarity	NPC476597
0.7778	Intermediate Similarity	NPC476601
0.7778	Intermediate Similarity	NPC169343
0.7778	Intermediate Similarity	NPC69143
0.7778	Intermediate Similarity	NPC476598
0.7778	Intermediate Similarity	NPC229976
0.7778	Intermediate Similarity	NPC40353
0.7765	Intermediate Similarity	NPC472440
0.7765	Intermediate Similarity	NPC477124
0.7765	Intermediate Similarity	NPC215893
0.7753	Intermediate Similarity	NPC472307
0.7753	Intermediate Similarity	NPC198818
0.7753	Intermediate Similarity	NPC477782
0.7753	Intermediate Similarity	NPC51486
0.7742	Intermediate Similarity	NPC252295
0.7742	Intermediate Similarity	NPC234617
0.7742	Intermediate Similarity	NPC124703
0.7742	Intermediate Similarity	NPC176845
0.7738	Intermediate Similarity	NPC223330
0.7738	Intermediate Similarity	NPC473420
0.7738	Intermediate Similarity	NPC149237
0.7738	Intermediate Similarity	NPC25554
0.7738	Intermediate Similarity	NPC475951
0.7738	Intermediate Similarity	NPC209318
0.7727	Intermediate Similarity	NPC97884
0.7727	Intermediate Similarity	NPC472220
0.7722	Intermediate Similarity	NPC160817
0.7722	Intermediate Similarity	NPC163003
0.7717	Intermediate Similarity	NPC322063
0.7711	Intermediate Similarity	NPC17550
0.7711	Intermediate Similarity	NPC89128
0.7711	Intermediate Similarity	NPC182550
0.7708	Intermediate Similarity	NPC258532
0.7701	Intermediate Similarity	NPC195640
0.7701	Intermediate Similarity	NPC477920
0.7701	Intermediate Similarity	NPC473226

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 NPC195424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1338
0.2-0.3	3989
0.3-0.4	2474
0.4-0.5	716
0.5-0.6	303
0.6-0.7	151
0.7-0.8	28
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD4752	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD1694	Approved
0.7875	Intermediate Similarity	NPD8039	Approved
0.7701	Intermediate Similarity	NPD7521	Approved
0.7701	Intermediate Similarity	NPD7334	Approved
0.7701	Intermediate Similarity	NPD6409	Approved
0.7701	Intermediate Similarity	NPD5330	Approved
0.7701	Intermediate Similarity	NPD6684	Approved
0.7701	Intermediate Similarity	NPD7146	Approved
0.7582	Intermediate Similarity	NPD6399	Phase 3
0.7528	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6903	Approved
0.7528	Intermediate Similarity	NPD6672	Approved
0.7528	Intermediate Similarity	NPD5737	Approved
0.7473	Intermediate Similarity	NPD5693	Phase 1
0.7363	Intermediate Similarity	NPD5207	Approved
0.7303	Intermediate Similarity	NPD6098	Approved
0.7253	Intermediate Similarity	NPD6051	Approved
0.7241	Intermediate Similarity	NPD3667	Approved
0.7234	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD5208	Approved
0.7128	Intermediate Similarity	NPD7900	Approved
0.7128	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6001	Approved
0.7079	Intermediate Similarity	NPD3668	Phase 3
0.7079	Intermediate Similarity	NPD4786	Approved
0.7065	Intermediate Similarity	NPD6080	Approved
0.7065	Intermediate Similarity	NPD6904	Approved
0.7065	Intermediate Similarity	NPD6673	Approved
0.7053	Intermediate Similarity	NPD5695	Phase 3
0.7033	Intermediate Similarity	NPD3573	Approved
0.701	Intermediate Similarity	NPD7638	Approved
0.701	Intermediate Similarity	NPD5696	Approved
0.6989	Remote Similarity	NPD5692	Phase 3
0.6947	Remote Similarity	NPD7748	Approved
0.6939	Remote Similarity	NPD7639	Approved
0.6939	Remote Similarity	NPD7640	Approved
0.6931	Remote Similarity	NPD6008	Approved
0.6923	Remote Similarity	NPD3618	Phase 1
0.6915	Remote Similarity	NPD5694	Approved
0.6915	Remote Similarity	NPD6050	Approved
0.6907	Remote Similarity	NPD7902	Approved
0.6907	Remote Similarity	NPD6084	Phase 2
0.6907	Remote Similarity	NPD6083	Phase 2
0.6889	Remote Similarity	NPD3665	Phase 1
0.6889	Remote Similarity	NPD3666	Approved
0.6889	Remote Similarity	NPD3133	Approved
0.6882	Remote Similarity	NPD1695	Approved
0.6875	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7115	Discovery
0.6739	Remote Similarity	NPD4623	Approved
0.6739	Remote Similarity	NPD4519	Discontinued
0.6737	Remote Similarity	NPD7515	Phase 2
0.6737	Remote Similarity	NPD5284	Approved
0.6737	Remote Similarity	NPD5281	Approved
0.6737	Remote Similarity	NPD6411	Approved
0.6699	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6635	Remote Similarity	NPD6686	Approved
0.6633	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5785	Approved
0.6629	Remote Similarity	NPD4695	Discontinued
0.6627	Remote Similarity	NPD4137	Phase 3
0.6569	Remote Similarity	NPD6052	Approved
0.6562	Remote Similarity	NPD8034	Phase 2
0.6562	Remote Similarity	NPD8035	Phase 2
0.6559	Remote Similarity	NPD5279	Phase 3
0.6548	Remote Similarity	NPD4747	Approved
0.6548	Remote Similarity	NPD4691	Approved
0.6531	Remote Similarity	NPD5654	Approved
0.6526	Remote Similarity	NPD5328	Approved
0.6526	Remote Similarity	NPD6101	Approved
0.6526	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4753	Phase 2
0.6522	Remote Similarity	NPD4197	Approved
0.6509	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5209	Approved
0.6452	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5329	Approved
0.6442	Remote Similarity	NPD6675	Approved
0.6442	Remote Similarity	NPD6402	Approved
0.6442	Remote Similarity	NPD7128	Approved
0.6442	Remote Similarity	NPD5739	Approved
0.6436	Remote Similarity	NPD6404	Discontinued
0.6415	Remote Similarity	NPD6372	Approved
0.6415	Remote Similarity	NPD6373	Approved
0.6415	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7154	Phase 3
0.6413	Remote Similarity	NPD5362	Discontinued
0.6404	Remote Similarity	NPD3617	Approved
0.6404	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5959	Approved
0.6392	Remote Similarity	NPD7637	Suspended
0.6392	Remote Similarity	NPD6079	Approved
0.6389	Remote Similarity	NPD6053	Discontinued
0.6383	Remote Similarity	NPD4694	Approved
0.6383	Remote Similarity	NPD4689	Approved
0.6383	Remote Similarity	NPD4693	Phase 3
0.6383	Remote Similarity	NPD5690	Phase 2
0.6383	Remote Similarity	NPD5280	Approved
0.6383	Remote Similarity	NPD4688	Approved
0.6383	Remote Similarity	NPD4690	Approved
0.6383	Remote Similarity	NPD5205	Approved
0.6383	Remote Similarity	NPD4138	Approved
0.6383	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5701	Approved
0.6381	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD5210	Approved
0.6364	Remote Similarity	NPD4629	Approved
0.6364	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4202	Approved
0.6322	Remote Similarity	NPD4687	Approved
0.6322	Remote Similarity	NPD4058	Approved
0.6322	Remote Similarity	NPD5733	Approved
0.6321	Remote Similarity	NPD6881	Approved
0.6321	Remote Similarity	NPD7320	Approved
0.6321	Remote Similarity	NPD6899	Approved
0.6321	Remote Similarity	NPD6011	Approved
0.6311	Remote Similarity	NPD7632	Discontinued
0.6304	Remote Similarity	NPD4269	Approved
0.6304	Remote Similarity	NPD4270	Approved
0.63	Remote Similarity	NPD7732	Phase 3
0.63	Remote Similarity	NPD4697	Phase 3
0.6296	Remote Similarity	NPD6649	Approved
0.6296	Remote Similarity	NPD6650	Approved
0.6289	Remote Similarity	NPD46	Approved
0.6289	Remote Similarity	NPD6698	Approved
0.6279	Remote Similarity	NPD5276	Approved
0.6279	Remote Similarity	NPD5777	Approved
0.6277	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6013	Approved
0.6262	Remote Similarity	NPD6012	Approved
0.6262	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD6942	Approved
0.6226	Remote Similarity	NPD6614	Approved
0.6211	Remote Similarity	NPD5786	Approved
0.6204	Remote Similarity	NPD6883	Approved
0.6204	Remote Similarity	NPD7290	Approved
0.6204	Remote Similarity	NPD7102	Approved
0.6196	Remote Similarity	NPD4139	Approved
0.6196	Remote Similarity	NPD4692	Approved
0.6196	Remote Similarity	NPD5369	Approved
0.6147	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD8130	Phase 1
0.6147	Remote Similarity	NPD6869	Approved
0.6147	Remote Similarity	NPD6617	Approved
0.6147	Remote Similarity	NPD6847	Approved
0.6139	Remote Similarity	NPD5222	Approved
0.6139	Remote Similarity	NPD5221	Approved
0.6139	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1696	Phase 3
0.6105	Remote Similarity	NPD5363	Approved
0.61	Remote Similarity	NPD5282	Discontinued
0.6091	Remote Similarity	NPD8297	Approved
0.6091	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD4252	Approved
0.6087	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5173	Approved
0.6078	Remote Similarity	NPD4755	Approved
0.6075	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6412	Phase 2
0.6067	Remote Similarity	NPD3702	Approved
0.6064	Remote Similarity	NPD4788	Approved
0.6055	Remote Similarity	NPD6371	Approved
0.6042	Remote Similarity	NPD6422	Discontinued
0.6036	Remote Similarity	NPD6858	Approved
0.6036	Remote Similarity	NPD7094	Approved
0.6022	Remote Similarity	NPD857	Phase 3
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6	Remote Similarity	NPD287	Approved
0.6	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7614	Phase 1
0.5979	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4195	Approved
0.5978	Remote Similarity	NPD7645	Phase 2
0.5962	Remote Similarity	NPD4696	Approved
0.5962	Remote Similarity	NPD4700	Approved
0.5962	Remote Similarity	NPD5285	Approved
0.5962	Remote Similarity	NPD5286	Approved
0.596	Remote Similarity	NPD4096	Approved
0.5957	Remote Similarity	NPD6435	Approved
0.5955	Remote Similarity	NPD4785	Approved
0.5955	Remote Similarity	NPD6924	Approved
0.5955	Remote Similarity	NPD6926	Approved
0.5955	Remote Similarity	NPD4784	Approved
0.5948	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5707	Approved
0.5929	Remote Similarity	NPD6274	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