NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.15
Volume:	257.918
LogP:	3.312
LogD:	3.328
LogS:	-3.49
# Rotatable Bonds:	2
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	4.593
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.482
MDCK Permeability:	5.599753785645589e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.593
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.312
Plasma Protein Binding (PPB):	71.14130401611328%
Volume Distribution (VD):	1.626
Pgp-substrate:	28.372516632080078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.709
CYP1A2-substrate:	0.424
CYP2C19-inhibitor:	0.26
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.34
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.831
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	14.014
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.131
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.538
Skin Sensitization:	0.521
Carcinogencity:	0.873
Eye Corrosion:	0.972
Eye Irritation:	0.926
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC38642

Natural Product ID:	NPC38642
*Common Name:**	Dehydrosaussurealactone
IUPAC Name:	(3aS,6S,7S,7aS)-6-ethenyl-6-methyl-3-methylidene-7-prop-1-en-2-yl-4,5,7,7a-tetrahydro-3aH-1-benzofuran-2-one
Synonyms:	Dehydrosaussurealactone
Standard InCHIKey:	ZNTHTBBAGNVESR-SFDCQRBFSA-N
Standard InCHI:	InChI=1S/C15H20O2/c1-6-15(5)8-7-11-10(4)14(16)17-13(11)12(15)9(2)3/h6,11-13H,1-2,4,7-8H2,3,5H3/t11-,12+,13-,15+/m0/s1
SMILES:	C=C[C@]1(C)CC[C@@H]2[C@@H]([C@H]1C(=C)C)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL205002
PubChem CID:	44409528
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20584613]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	Species	Asteraceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	100.0	uM	PMID[524798]

☑ 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 NPC38642 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	169
0.1-0.2	1306
0.2-0.3	5569
0.3-0.4	14219
0.4-0.5	8603
0.5-0.6	7254
0.6-0.7	4858
0.7-0.8	654
0.8-0.85	41
0.85-0.9	19
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC226988
0.9241	High Similarity	NPC194637
0.9146	High Similarity	NPC215831
0.9125	High Similarity	NPC470011
0.9125	High Similarity	NPC219011
0.9036	High Similarity	NPC73995
0.8902	High Similarity	NPC85698
0.8902	High Similarity	NPC9231
0.8902	High Similarity	NPC477920
0.8795	High Similarity	NPC470012
0.8795	High Similarity	NPC175293
0.8795	High Similarity	NPC181103
0.8795	High Similarity	NPC305029
0.8706	High Similarity	NPC152467
0.869	High Similarity	NPC477128
0.8642	High Similarity	NPC178676
0.8621	High Similarity	NPC471446
0.8621	High Similarity	NPC477129
0.8621	High Similarity	NPC473434
0.8621	High Similarity	NPC474841
0.8621	High Similarity	NPC477130
0.8605	High Similarity	NPC233345
0.8605	High Similarity	NPC186363
0.859	High Similarity	NPC92489
0.8588	High Similarity	NPC288699
0.8588	High Similarity	NPC116620
0.8554	High Similarity	NPC177932
0.8537	High Similarity	NPC22611
0.8488	Intermediate Similarity	NPC475776
0.8452	Intermediate Similarity	NPC185638
0.8427	Intermediate Similarity	NPC284518
0.8395	Intermediate Similarity	NPC195424
0.8333	Intermediate Similarity	NPC110405
0.8315	Intermediate Similarity	NPC183012
0.8293	Intermediate Similarity	NPC475665
0.8293	Intermediate Similarity	NPC475951
0.8293	Intermediate Similarity	NPC223330
0.8293	Intermediate Similarity	NPC209318
0.8256	Intermediate Similarity	NPC277771
0.8256	Intermediate Similarity	NPC226863
0.8222	Intermediate Similarity	NPC228766
0.8222	Intermediate Similarity	NPC165528
0.8222	Intermediate Similarity	NPC307164
0.8214	Intermediate Similarity	NPC139566
0.8202	Intermediate Similarity	NPC469596
0.8202	Intermediate Similarity	NPC148000
0.8202	Intermediate Similarity	NPC24861
0.8202	Intermediate Similarity	NPC225474
0.8193	Intermediate Similarity	NPC186276
0.8182	Intermediate Similarity	NPC49420
0.8148	Intermediate Similarity	NPC184737
0.8148	Intermediate Similarity	NPC35574
0.8125	Intermediate Similarity	NPC41017
0.8111	Intermediate Similarity	NPC90014
0.8111	Intermediate Similarity	NPC56369
0.8111	Intermediate Similarity	NPC157686
0.8111	Intermediate Similarity	NPC259042
0.8095	Intermediate Similarity	NPC193198
0.809	Intermediate Similarity	NPC475657
0.8072	Intermediate Similarity	NPC47635
0.8068	Intermediate Similarity	NPC153853
0.8068	Intermediate Similarity	NPC158488
0.8068	Intermediate Similarity	NPC220454
0.8068	Intermediate Similarity	NPC212679
0.8068	Intermediate Similarity	NPC469595
0.8065	Intermediate Similarity	NPC308824
0.8049	Intermediate Similarity	NPC263951
0.8043	Intermediate Similarity	NPC252295
0.8043	Intermediate Similarity	NPC216478
0.8025	Intermediate Similarity	NPC41780
0.8025	Intermediate Similarity	NPC187568
0.8023	Intermediate Similarity	NPC6979
0.8022	Intermediate Similarity	NPC93245
0.8022	Intermediate Similarity	NPC473964
0.8	Intermediate Similarity	NPC470697
0.8	Intermediate Similarity	NPC159635
0.8	Intermediate Similarity	NPC30486
0.8	Intermediate Similarity	NPC97505
0.7979	Intermediate Similarity	NPC164551
0.7976	Intermediate Similarity	NPC123880
0.7976	Intermediate Similarity	NPC471159
0.7957	Intermediate Similarity	NPC476303
0.7957	Intermediate Similarity	NPC47024
0.7957	Intermediate Similarity	NPC470906
0.7955	Intermediate Similarity	NPC168131
0.7952	Intermediate Similarity	NPC73052
0.7952	Intermediate Similarity	NPC6823
0.7952	Intermediate Similarity	NPC290508
0.7952	Intermediate Similarity	NPC293418
0.7935	Intermediate Similarity	NPC474921
0.7935	Intermediate Similarity	NPC473963
0.7935	Intermediate Similarity	NPC136781
0.7907	Intermediate Similarity	NPC33570
0.7907	Intermediate Similarity	NPC52628
0.7907	Intermediate Similarity	NPC189311
0.7907	Intermediate Similarity	NPC21471
0.7907	Intermediate Similarity	NPC161957
0.7901	Intermediate Similarity	NPC235906
0.7895	Intermediate Similarity	NPC156681
0.7889	Intermediate Similarity	NPC475700
0.7882	Intermediate Similarity	NPC470948
0.7875	Intermediate Similarity	NPC320537
0.7875	Intermediate Similarity	NPC143979
0.7872	Intermediate Similarity	NPC242666
0.7865	Intermediate Similarity	NPC469372
0.7865	Intermediate Similarity	NPC8062
0.7849	Intermediate Similarity	NPC473155
0.7831	Intermediate Similarity	NPC182550
0.7816	Intermediate Similarity	NPC471042
0.7816	Intermediate Similarity	NPC250981
0.7805	Intermediate Similarity	NPC476794
0.7805	Intermediate Similarity	NPC470240
0.7805	Intermediate Similarity	NPC65603
0.7802	Intermediate Similarity	NPC250075
0.7802	Intermediate Similarity	NPC38830
0.7802	Intermediate Similarity	NPC66581
0.7792	Intermediate Similarity	NPC469868
0.7778	Intermediate Similarity	NPC303697
0.7778	Intermediate Similarity	NPC226669
0.7778	Intermediate Similarity	NPC252433
0.7778	Intermediate Similarity	NPC72845
0.7778	Intermediate Similarity	NPC193351
0.7778	Intermediate Similarity	NPC155587
0.7778	Intermediate Similarity	NPC65513
0.7778	Intermediate Similarity	NPC138408
0.7765	Intermediate Similarity	NPC476458
0.7765	Intermediate Similarity	NPC258153
0.7765	Intermediate Similarity	NPC200513
0.7753	Intermediate Similarity	NPC50488
0.7753	Intermediate Similarity	NPC474396
0.7753	Intermediate Similarity	NPC194642
0.7753	Intermediate Similarity	NPC173042
0.7742	Intermediate Similarity	NPC110937
0.7742	Intermediate Similarity	NPC38530
0.7742	Intermediate Similarity	NPC474343
0.7742	Intermediate Similarity	NPC84335
0.7738	Intermediate Similarity	NPC276356
0.7732	Intermediate Similarity	NPC477125
0.7727	Intermediate Similarity	NPC312561
0.7717	Intermediate Similarity	NPC33473
0.7717	Intermediate Similarity	NPC280877
0.7708	Intermediate Similarity	NPC176883
0.7708	Intermediate Similarity	NPC254202
0.7708	Intermediate Similarity	NPC476237
0.7692	Intermediate Similarity	NPC166346
0.7692	Intermediate Similarity	NPC474185
0.7692	Intermediate Similarity	NPC139692
0.7684	Intermediate Similarity	NPC111292
0.7684	Intermediate Similarity	NPC475958
0.7674	Intermediate Similarity	NPC54468
0.7674	Intermediate Similarity	NPC39588
0.7674	Intermediate Similarity	NPC215294
0.7674	Intermediate Similarity	NPC170862
0.7674	Intermediate Similarity	NPC222358
0.7667	Intermediate Similarity	NPC475965
0.7667	Intermediate Similarity	NPC474842
0.766	Intermediate Similarity	NPC176845
0.766	Intermediate Similarity	NPC476806
0.766	Intermediate Similarity	NPC316598
0.766	Intermediate Similarity	NPC476807
0.766	Intermediate Similarity	NPC23364
0.764	Intermediate Similarity	NPC477302
0.764	Intermediate Similarity	NPC136879
0.764	Intermediate Similarity	NPC474845
0.7634	Intermediate Similarity	NPC112654
0.7629	Intermediate Similarity	NPC189616
0.7629	Intermediate Similarity	NPC477127
0.7625	Intermediate Similarity	NPC163003
0.7619	Intermediate Similarity	NPC472965
0.7619	Intermediate Similarity	NPC471475
0.7619	Intermediate Similarity	NPC264227
0.7619	Intermediate Similarity	NPC470239
0.7619	Intermediate Similarity	NPC617
0.7619	Intermediate Similarity	NPC63649
0.7619	Intermediate Similarity	NPC470244
0.7614	Intermediate Similarity	NPC329692
0.7614	Intermediate Similarity	NPC220478
0.7609	Intermediate Similarity	NPC84893
0.7609	Intermediate Similarity	NPC57117
0.7595	Intermediate Similarity	NPC199557
0.759	Intermediate Similarity	NPC208223
0.759	Intermediate Similarity	NPC316500
0.7586	Intermediate Similarity	NPC149869
0.7586	Intermediate Similarity	NPC100391
0.7586	Intermediate Similarity	NPC475100
0.7586	Intermediate Similarity	NPC96055
0.7579	Intermediate Similarity	NPC474012
0.7579	Intermediate Similarity	NPC476299
0.7579	Intermediate Similarity	NPC470761
0.7579	Intermediate Similarity	NPC473219
0.7561	Intermediate Similarity	NPC39362
0.7556	Intermediate Similarity	NPC5509
0.7556	Intermediate Similarity	NPC206001
0.7556	Intermediate Similarity	NPC284561
0.7556	Intermediate Similarity	NPC218927
0.7553	Intermediate Similarity	NPC70145
0.7553	Intermediate Similarity	NPC474395
0.7553	Intermediate Similarity	NPC91695
0.7553	Intermediate Similarity	NPC10057
0.7553	Intermediate Similarity	NPC2049

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 NPC38642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1737
0.2-0.3	4013
0.3-0.4	2183
0.4-0.5	627
0.5-0.6	265
0.6-0.7	153
0.7-0.8	13
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8554	High Similarity	NPD1694	Approved
0.7765	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4225	Approved
0.7222	Intermediate Similarity	NPD7146	Approved
0.7222	Intermediate Similarity	NPD7334	Approved
0.7222	Intermediate Similarity	NPD7521	Approved
0.7222	Intermediate Similarity	NPD5330	Approved
0.7222	Intermediate Similarity	NPD6409	Approved
0.7222	Intermediate Similarity	NPD6684	Approved
0.7158	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3573	Approved
0.7065	Intermediate Similarity	NPD6903	Approved
0.7065	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7900	Approved
0.7021	Intermediate Similarity	NPD8035	Phase 2
0.7021	Intermediate Similarity	NPD8034	Phase 2
0.6989	Remote Similarity	NPD1695	Approved
0.6979	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6399	Phase 3
0.6941	Remote Similarity	NPD8039	Approved
0.6939	Remote Similarity	NPD7638	Approved
0.6923	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5207	Approved
0.6882	Remote Similarity	NPD5737	Approved
0.6882	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD6001	Approved
0.6875	Remote Similarity	NPD7748	Approved
0.6869	Remote Similarity	NPD7639	Approved
0.6869	Remote Similarity	NPD7640	Approved
0.6863	Remote Similarity	NPD6008	Approved
0.6852	Remote Similarity	NPD7115	Discovery
0.6848	Remote Similarity	NPD3618	Phase 1
0.6842	Remote Similarity	NPD5693	Phase 1
0.6837	Remote Similarity	NPD7902	Approved
0.6737	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD6079	Approved
0.6635	Remote Similarity	NPD5697	Approved
0.6593	Remote Similarity	NPD5209	Approved
0.6593	Remote Similarity	NPD3667	Approved
0.6571	Remote Similarity	NPD6011	Approved
0.6571	Remote Similarity	NPD6899	Approved
0.6571	Remote Similarity	NPD6881	Approved
0.6542	Remote Similarity	NPD6650	Approved
0.6542	Remote Similarity	NPD6649	Approved
0.6526	Remote Similarity	NPD5208	Approved
0.6509	Remote Similarity	NPD6013	Approved
0.6509	Remote Similarity	NPD6014	Approved
0.6509	Remote Similarity	NPD6012	Approved
0.6495	Remote Similarity	NPD6411	Approved
0.6495	Remote Similarity	NPD5694	Approved
0.6489	Remote Similarity	NPD6098	Approved
0.6476	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5695	Phase 3
0.6458	Remote Similarity	NPD6673	Approved
0.6458	Remote Similarity	NPD6080	Approved
0.6458	Remote Similarity	NPD6051	Approved
0.6458	Remote Similarity	NPD6904	Approved
0.6458	Remote Similarity	NPD5328	Approved
0.6452	Remote Similarity	NPD3668	Phase 3
0.6452	Remote Similarity	NPD3666	Approved
0.6452	Remote Similarity	NPD4786	Approved
0.6452	Remote Similarity	NPD3665	Phase 1
0.6452	Remote Similarity	NPD3133	Approved
0.6449	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD7290	Approved
0.6449	Remote Similarity	NPD7102	Approved
0.6436	Remote Similarity	NPD5696	Approved
0.6415	Remote Similarity	NPD6686	Approved
0.6415	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5222	Approved
0.64	Remote Similarity	NPD5221	Approved
0.6395	Remote Similarity	NPD5777	Approved
0.6392	Remote Similarity	NPD5692	Phase 3
0.6389	Remote Similarity	NPD8130	Phase 1
0.6389	Remote Similarity	NPD6869	Approved
0.6389	Remote Similarity	NPD6847	Approved
0.6389	Remote Similarity	NPD6617	Approved
0.6381	Remote Similarity	NPD6402	Approved
0.6381	Remote Similarity	NPD5739	Approved
0.6381	Remote Similarity	NPD6675	Approved
0.6381	Remote Similarity	NPD7128	Approved
0.6355	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD6373	Approved
0.6344	Remote Similarity	NPD4788	Approved
0.6337	Remote Similarity	NPD6084	Phase 2
0.6337	Remote Similarity	NPD6083	Phase 2
0.6337	Remote Similarity	NPD5173	Approved
0.633	Remote Similarity	NPD6882	Approved
0.633	Remote Similarity	NPD8297	Approved
0.6327	Remote Similarity	NPD6050	Approved
0.6327	Remote Similarity	NPD5284	Approved
0.6327	Remote Similarity	NPD5281	Approved
0.6321	Remote Similarity	NPD5701	Approved
0.6316	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6101	Approved
0.6263	Remote Similarity	NPD4202	Approved
0.6263	Remote Similarity	NPD5778	Approved
0.6263	Remote Similarity	NPD5779	Approved
0.6262	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD5211	Phase 2
0.6238	Remote Similarity	NPD4697	Phase 3
0.6235	Remote Similarity	NPD229	Approved
0.6214	Remote Similarity	NPD5285	Approved
0.6214	Remote Similarity	NPD5286	Approved
0.6214	Remote Similarity	NPD4696	Approved
0.6211	Remote Similarity	NPD5363	Approved
0.6204	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5282	Discontinued
0.6196	Remote Similarity	NPD4695	Discontinued
0.6174	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7154	Phase 3
0.617	Remote Similarity	NPD5362	Discontinued
0.6161	Remote Similarity	NPD6868	Approved
0.6154	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5223	Approved
0.6146	Remote Similarity	NPD4519	Discontinued
0.6146	Remote Similarity	NPD5690	Phase 2
0.6146	Remote Similarity	NPD4623	Approved
0.6146	Remote Similarity	NPD5279	Phase 3
0.6139	Remote Similarity	NPD5210	Approved
0.6139	Remote Similarity	NPD4629	Approved
0.6132	Remote Similarity	NPD5141	Approved
0.6129	Remote Similarity	NPD5369	Approved
0.6126	Remote Similarity	NPD4632	Approved
0.6111	Remote Similarity	NPD6117	Approved
0.6106	Remote Similarity	NPD6317	Approved
0.6095	Remote Similarity	NPD5226	Approved
0.6095	Remote Similarity	NPD5225	Approved
0.6095	Remote Similarity	NPD4633	Approved
0.6095	Remote Similarity	NPD5224	Approved
0.6092	Remote Similarity	NPD4691	Approved
0.6091	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4058	Approved
0.6064	Remote Similarity	NPD4221	Approved
0.6064	Remote Similarity	NPD4223	Phase 3
0.6064	Remote Similarity	NPD4270	Approved
0.6064	Remote Similarity	NPD4269	Approved
0.6061	Remote Similarity	NPD6698	Approved
0.6061	Remote Similarity	NPD46	Approved
0.6058	Remote Similarity	NPD6648	Approved
0.6053	Remote Similarity	NPD6314	Approved
0.6053	Remote Similarity	NPD6335	Approved
0.6053	Remote Similarity	NPD6313	Approved
0.6044	Remote Similarity	NPD6116	Phase 1
0.6038	Remote Similarity	NPD6052	Approved
0.6038	Remote Similarity	NPD5174	Approved
0.6038	Remote Similarity	NPD5175	Approved
0.6019	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4755	Approved
0.6019	Remote Similarity	NPD6614	Approved
0.6018	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD6371	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD3702	Approved
0.6	Remote Similarity	NPD5344	Discontinued
0.5982	Remote Similarity	NPD8133	Approved
0.598	Remote Similarity	NPD5654	Approved
0.5979	Remote Similarity	NPD5786	Approved
0.5978	Remote Similarity	NPD6697	Approved
0.5978	Remote Similarity	NPD6114	Approved
0.5978	Remote Similarity	NPD6115	Approved
0.5978	Remote Similarity	NPD6118	Approved
0.5977	Remote Similarity	NPD4137	Phase 3
0.5976	Remote Similarity	NPD1145	Discontinued
0.5965	Remote Similarity	NPD6009	Approved
0.596	Remote Similarity	NPD4753	Phase 2
0.596	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6319	Approved
0.5938	Remote Similarity	NPD4197	Approved
0.5922	Remote Similarity	NPD7732	Phase 3
0.5909	Remote Similarity	NPD4747	Approved
0.5905	Remote Similarity	NPD4700	Approved
0.5897	Remote Similarity	NPD5983	Phase 2
0.5895	Remote Similarity	NPD6435	Approved
0.5893	Remote Similarity	NPD6053	Discontinued
0.5889	Remote Similarity	NPD4687	Approved
0.5882	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7492	Approved
0.5876	Remote Similarity	NPD5329	Approved
0.5876	Remote Similarity	NPD1696	Phase 3
0.5876	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5959	Approved
0.5854	Remote Similarity	NPD7260	Phase 2
0.5851	Remote Similarity	NPD4252	Approved
0.5851	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6858	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