NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	263.425
LogP:	2.525
LogD:	2.56
LogS:	-3.462
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	4.424
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.545
MDCK Permeability:	2.7220761694479734e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.33
Plasma Protein Binding (PPB):	69.16144561767578%
Volume Distribution (VD):	0.828
Pgp-substrate:	20.694955825805664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.429
CYP1A2-substrate:	0.527
CYP2C19-inhibitor:	0.273
CYP2C19-substrate:	0.792
CYP2C9-inhibitor:	0.164
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.23
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.278
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	7.96
Half-life (T1/2):	0.224

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.329
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.859
Maximum Recommended Daily Dose:	0.118
Skin Sensitization:	0.65
Carcinogencity:	0.632
Eye Corrosion:	0.93
Eye Irritation:	0.958
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC9231

Natural Product ID:	NPC9231
*Common Name:**	Arbusculin A
IUPAC Name:	(3aS,5aR,9R,9aS,9bS)-9-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
Synonyms:
Standard InCHIKey:	BVRDNJZFYKHRJQ-CWFCOSEVSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9-10-5-8-14(2)6-4-7-15(3,17)12(14)11(10)18-13(9)16/h10-12,17H,1,4-8H2,2-3H3/t10-,11-,12+,14+,15+/m0/s1
SMILES:	C=C1C(=O)O[C@H]2[C@H]1CC[C@@]1([C@@H]2[C@](C)(O)CCC1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446602
PubChem CID:	160153
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30115	Aucklandia lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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	9

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	Inhibition	=	2.0	%	PMID[456047]
NPT168	Cell Line	P388	Mus musculus	Inhibition	=	45.0	%	PMID[456047]
NPT168	Cell Line	P388	Mus musculus	Inhibition	=	101.0	%	PMID[456047]
NPT377	Cell Line	OVCAR-3	Homo sapiens	CD50	=	7.5	ug ml-1	PMID[456048]
NPT165	Cell Line	HeLa	Homo sapiens	CD50	=	7.5	ug ml-1	PMID[456048]
NPT65	Cell Line	HepG2	Homo sapiens	CD50	=	10.0	ug ml-1	PMID[456048]
NPT168	Cell Line	P388	Mus musculus	GI	=	45.0	%	PMID[456049]
NPT168	Cell Line	P388	Mus musculus	GI	=	101.0	%	PMID[456049]
NPT168	Cell Line	P388	Mus musculus	GI	=	2.0	%	PMID[456049]

☑ 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 NPC9231 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	175
0.1-0.2	1266
0.2-0.3	5035
0.3-0.4	12450
0.4-0.5	9348
0.5-0.6	6552
0.6-0.7	6169
0.7-0.8	1579
0.8-0.85	81
0.85-0.9	29
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC85698
0.9398	High Similarity	NPC305029
0.9398	High Similarity	NPC181103
0.9259	High Similarity	NPC226988
0.9176	High Similarity	NPC116620
0.9048	High Similarity	NPC185638
0.9048	High Similarity	NPC477920
0.8989	High Similarity	NPC93245
0.8989	High Similarity	NPC473964
0.8977	High Similarity	NPC24861
0.8977	High Similarity	NPC148000
0.8977	High Similarity	NPC225474
0.8977	High Similarity	NPC469596
0.8941	High Similarity	NPC470012
0.8902	High Similarity	NPC38642
0.8902	High Similarity	NPC209318
0.8902	High Similarity	NPC223330
0.8889	High Similarity	NPC136781
0.8889	High Similarity	NPC263951
0.8889	High Similarity	NPC473963
0.8876	High Similarity	NPC157686
0.8876	High Similarity	NPC90014
0.8876	High Similarity	NPC259042
0.875	High Similarity	NPC233345
0.875	High Similarity	NPC186363
0.8721	High Similarity	NPC175293
0.869	High Similarity	NPC194637
0.8636	High Similarity	NPC475776
0.8621	High Similarity	NPC277771
0.8602	High Similarity	NPC475958
0.8588	High Similarity	NPC219011
0.8588	High Similarity	NPC97505
0.8588	High Similarity	NPC470011
0.8523	High Similarity	NPC194642
0.8519	High Similarity	NPC92489
0.8495	Intermediate Similarity	NPC47024
0.8462	Intermediate Similarity	NPC183012
0.8462	Intermediate Similarity	NPC56369
0.8452	Intermediate Similarity	NPC475951
0.8421	Intermediate Similarity	NPC61442
0.8409	Intermediate Similarity	NPC215831
0.8395	Intermediate Similarity	NPC39362
0.8387	Intermediate Similarity	NPC216478
0.8387	Intermediate Similarity	NPC476807
0.8387	Intermediate Similarity	NPC473155
0.8387	Intermediate Similarity	NPC476806
0.837	Intermediate Similarity	NPC228766
0.837	Intermediate Similarity	NPC165528
0.837	Intermediate Similarity	NPC284518
0.8353	Intermediate Similarity	NPC123880
0.8353	Intermediate Similarity	NPC471159
0.8333	Intermediate Similarity	NPC72845
0.8315	Intermediate Similarity	NPC73995
0.8298	Intermediate Similarity	NPC476303
0.828	Intermediate Similarity	NPC474921
0.8256	Intermediate Similarity	NPC243347
0.8242	Intermediate Similarity	NPC139692
0.8242	Intermediate Similarity	NPC147272
0.8229	Intermediate Similarity	NPC72842
0.8229	Intermediate Similarity	NPC99510
0.8222	Intermediate Similarity	NPC158488
0.8222	Intermediate Similarity	NPC152467
0.8182	Intermediate Similarity	NPC6979
0.8182	Intermediate Similarity	NPC250981
0.8161	Intermediate Similarity	NPC130966
0.8152	Intermediate Similarity	NPC471446
0.8152	Intermediate Similarity	NPC66581
0.8152	Intermediate Similarity	NPC474841
0.8152	Intermediate Similarity	NPC473434
0.8144	Intermediate Similarity	NPC283850
0.814	Intermediate Similarity	NPC178676
0.8132	Intermediate Similarity	NPC49420
0.8132	Intermediate Similarity	NPC252433
0.8125	Intermediate Similarity	NPC164551
0.8125	Intermediate Similarity	NPC476081
0.8111	Intermediate Similarity	NPC168131
0.8111	Intermediate Similarity	NPC50488
0.8111	Intermediate Similarity	NPC474396
0.809	Intermediate Similarity	NPC476932
0.8085	Intermediate Similarity	NPC474343
0.8081	Intermediate Similarity	NPC255082
0.8072	Intermediate Similarity	NPC476601
0.8068	Intermediate Similarity	NPC52628
0.8065	Intermediate Similarity	NPC210214
0.8061	Intermediate Similarity	NPC477125
0.8046	Intermediate Similarity	NPC470948
0.8046	Intermediate Similarity	NPC22611
0.8046	Intermediate Similarity	NPC471037
0.8043	Intermediate Similarity	NPC294263
0.8041	Intermediate Similarity	NPC120321
0.8041	Intermediate Similarity	NPC176883
0.8041	Intermediate Similarity	NPC476237
0.8022	Intermediate Similarity	NPC153853
0.8021	Intermediate Similarity	NPC242666
0.8021	Intermediate Similarity	NPC308824
0.8	Intermediate Similarity	NPC477302
0.8	Intermediate Similarity	NPC136879
0.8	Intermediate Similarity	NPC316598
0.8	Intermediate Similarity	NPC50847
0.8	Intermediate Similarity	NPC477128
0.798	Intermediate Similarity	NPC78966
0.798	Intermediate Similarity	NPC284732
0.7979	Intermediate Similarity	NPC134072
0.7979	Intermediate Similarity	NPC307164
0.7979	Intermediate Similarity	NPC234993
0.7979	Intermediate Similarity	NPC242848
0.7979	Intermediate Similarity	NPC13949
0.7979	Intermediate Similarity	NPC29952
0.7978	Intermediate Similarity	NPC329692
0.7978	Intermediate Similarity	NPC472505
0.7976	Intermediate Similarity	NPC474433
0.7957	Intermediate Similarity	NPC477129
0.7957	Intermediate Similarity	NPC477130
0.7957	Intermediate Similarity	NPC250075
0.7957	Intermediate Similarity	NPC57117
0.7935	Intermediate Similarity	NPC472814
0.7935	Intermediate Similarity	NPC250753
0.7935	Intermediate Similarity	NPC303697
0.7935	Intermediate Similarity	NPC177037
0.7931	Intermediate Similarity	NPC258153
0.7931	Intermediate Similarity	NPC476458
0.7917	Intermediate Similarity	NPC471413
0.7917	Intermediate Similarity	NPC474012
0.7917	Intermediate Similarity	NPC476299
0.7912	Intermediate Similarity	NPC288699
0.7912	Intermediate Similarity	NPC174342
0.7912	Intermediate Similarity	NPC253618
0.7912	Intermediate Similarity	NPC218927
0.7912	Intermediate Similarity	NPC206001
0.7912	Intermediate Similarity	NPC77001
0.7907	Intermediate Similarity	NPC195424
0.7901	Intermediate Similarity	NPC235586
0.79	Intermediate Similarity	NPC37628
0.7895	Intermediate Similarity	NPC474395
0.7895	Intermediate Similarity	NPC73911
0.7889	Intermediate Similarity	NPC201658
0.7889	Intermediate Similarity	NPC171722
0.7872	Intermediate Similarity	NPC316215
0.7865	Intermediate Similarity	NPC329738
0.7865	Intermediate Similarity	NPC110405
0.7865	Intermediate Similarity	NPC177932
0.7865	Intermediate Similarity	NPC86316
0.7865	Intermediate Similarity	NPC106416
0.7865	Intermediate Similarity	NPC476602
0.7865	Intermediate Similarity	NPC65661
0.7857	Intermediate Similarity	NPC180204
0.7857	Intermediate Similarity	NPC36688
0.7857	Intermediate Similarity	NPC156681
0.7857	Intermediate Similarity	NPC112009
0.7849	Intermediate Similarity	NPC475700
0.7849	Intermediate Similarity	NPC472871
0.7849	Intermediate Similarity	NPC166346
0.7849	Intermediate Similarity	NPC115021
0.7841	Intermediate Similarity	NPC245665
0.7835	Intermediate Similarity	NPC235142
0.7835	Intermediate Similarity	NPC471412
0.7835	Intermediate Similarity	NPC111292
0.7822	Intermediate Similarity	NPC474243
0.7816	Intermediate Similarity	NPC232625
0.7816	Intermediate Similarity	NPC48673
0.7816	Intermediate Similarity	NPC20096
0.7816	Intermediate Similarity	NPC475665
0.7812	Intermediate Similarity	NPC278386
0.7812	Intermediate Similarity	NPC159763
0.7812	Intermediate Similarity	NPC252295
0.7812	Intermediate Similarity	NPC78427
0.7812	Intermediate Similarity	NPC124512
0.7812	Intermediate Similarity	NPC16911
0.7812	Intermediate Similarity	NPC234617
0.7812	Intermediate Similarity	NPC23364
0.7812	Intermediate Similarity	NPC124703
0.7802	Intermediate Similarity	NPC226863
0.78	Intermediate Similarity	NPC187435
0.78	Intermediate Similarity	NPC302788
0.78	Intermediate Similarity	NPC110496
0.78	Intermediate Similarity	NPC67321
0.7789	Intermediate Similarity	NPC472362
0.7789	Intermediate Similarity	NPC154526
0.7789	Intermediate Similarity	NPC104568
0.7789	Intermediate Similarity	NPC472363
0.7778	Intermediate Similarity	NPC296950
0.7778	Intermediate Similarity	NPC146731
0.7778	Intermediate Similarity	NPC471042
0.7766	Intermediate Similarity	NPC470697
0.7765	Intermediate Similarity	NPC307865
0.7755	Intermediate Similarity	NPC58329
0.7755	Intermediate Similarity	NPC32577
0.7755	Intermediate Similarity	NPC114540
0.7755	Intermediate Similarity	NPC155332
0.7755	Intermediate Similarity	NPC162973
0.7753	Intermediate Similarity	NPC159635
0.7753	Intermediate Similarity	NPC156485
0.7753	Intermediate Similarity	NPC139566
0.7732	Intermediate Similarity	NPC470906
0.7732	Intermediate Similarity	NPC201406
0.7732	Intermediate Similarity	NPC287676
0.7727	Intermediate Similarity	NPC186276
0.7723	Intermediate Similarity	NPC275539
0.7723	Intermediate Similarity	NPC306265
0.7723	Intermediate Similarity	NPC189075

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 NPC9231 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1651
0.2-0.3	3906
0.3-0.4	2279
0.4-0.5	675
0.5-0.6	203
0.6-0.7	213
0.7-0.8	62
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
0.7865	Intermediate Similarity	NPD1694	Approved
0.7812	Intermediate Similarity	NPD4225	Approved
0.7553	Intermediate Similarity	NPD8035	Phase 2
0.7553	Intermediate Similarity	NPD8034	Phase 2
0.7528	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7115	Discovery
0.7292	Intermediate Similarity	NPD6399	Phase 3
0.7273	Intermediate Similarity	NPD7638	Approved
0.7216	Intermediate Similarity	NPD7748	Approved
0.7204	Intermediate Similarity	NPD3618	Phase 1
0.72	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD7639	Approved
0.7172	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5697	Approved
0.71	Intermediate Similarity	NPD5696	Approved
0.7075	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4788	Approved
0.7048	Intermediate Similarity	NPD6881	Approved
0.7048	Intermediate Similarity	NPD6899	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
0.7019	Intermediate Similarity	NPD7128	Approved
0.7019	Intermediate Similarity	NPD5739	Approved
0.7019	Intermediate Similarity	NPD6675	Approved
0.7019	Intermediate Similarity	NPD6402	Approved
0.701	Intermediate Similarity	NPD7515	Phase 2
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.6981	Remote Similarity	NPD6012	Approved
0.6981	Remote Similarity	NPD6013	Approved
0.6981	Remote Similarity	NPD6372	Approved
0.6981	Remote Similarity	NPD6014	Approved
0.6981	Remote Similarity	NPD6373	Approved
0.6981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5695	Phase 3
0.6957	Remote Similarity	NPD3667	Approved
0.6952	Remote Similarity	NPD5701	Approved
0.6947	Remote Similarity	NPD3573	Approved
0.6916	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD7102	Approved
0.6887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6011	Approved
0.6887	Remote Similarity	NPD7320	Approved
0.6887	Remote Similarity	NPD6686	Approved
0.6875	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6903	Approved
0.6869	Remote Similarity	NPD7900	Approved
0.6869	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6001	Approved
0.6857	Remote Similarity	NPD6008	Approved
0.6852	Remote Similarity	NPD6617	Approved
0.6852	Remote Similarity	NPD6869	Approved
0.6852	Remote Similarity	NPD8130	Phase 1
0.6852	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5693	Phase 1
0.6837	Remote Similarity	NPD6079	Approved
0.6809	Remote Similarity	NPD3666	Approved
0.6809	Remote Similarity	NPD4786	Approved
0.6809	Remote Similarity	NPD3665	Phase 1
0.6809	Remote Similarity	NPD3133	Approved
0.6804	Remote Similarity	NPD5328	Approved
0.6804	Remote Similarity	NPD1695	Approved
0.6792	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6882	Approved
0.6789	Remote Similarity	NPD8297	Approved
0.6768	Remote Similarity	NPD4202	Approved
0.6742	Remote Similarity	NPD3702	Approved
0.6737	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7632	Discontinued
0.6731	Remote Similarity	NPD5211	Phase 2
0.6727	Remote Similarity	NPD8133	Approved
0.6701	Remote Similarity	NPD5737	Approved
0.6701	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD5286	Approved
0.6699	Remote Similarity	NPD5285	Approved
0.6699	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6634	Remote Similarity	NPD4629	Approved
0.6634	Remote Similarity	NPD5210	Approved
0.6633	Remote Similarity	NPD4753	Phase 2
0.6629	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6274	Approved
0.6604	Remote Similarity	NPD5141	Approved
0.6596	Remote Similarity	NPD4223	Phase 3
0.6596	Remote Similarity	NPD4221	Approved
0.6593	Remote Similarity	NPD6116	Phase 1
0.6571	Remote Similarity	NPD5225	Approved
0.6571	Remote Similarity	NPD4633	Approved
0.6571	Remote Similarity	NPD5224	Approved
0.6571	Remote Similarity	NPD5226	Approved
0.6569	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4697	Phase 3
0.6569	Remote Similarity	NPD5221	Approved
0.6569	Remote Similarity	NPD5222	Approved
0.6566	Remote Similarity	NPD5785	Approved
0.6566	Remote Similarity	NPD5207	Approved
0.6559	Remote Similarity	NPD4695	Discontinued
0.6545	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4700	Approved
0.6531	Remote Similarity	NPD5208	Approved
0.6522	Remote Similarity	NPD6114	Approved
0.6522	Remote Similarity	NPD6115	Approved
0.6522	Remote Similarity	NPD6697	Approved
0.6522	Remote Similarity	NPD6118	Approved
0.6509	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD5174	Approved
0.6505	Remote Similarity	NPD5173	Approved
0.65	Remote Similarity	NPD5281	Approved
0.65	Remote Similarity	NPD5284	Approved
0.6495	Remote Similarity	NPD4623	Approved
0.6495	Remote Similarity	NPD4519	Discontinued
0.6495	Remote Similarity	NPD6098	Approved
0.6476	Remote Similarity	NPD5223	Approved
0.6466	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6673	Approved
0.6465	Remote Similarity	NPD6904	Approved
0.6465	Remote Similarity	NPD6101	Approved
0.6465	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6080	Approved
0.6465	Remote Similarity	NPD6051	Approved
0.6458	Remote Similarity	NPD4197	Approved
0.6458	Remote Similarity	NPD3668	Phase 3
0.6436	Remote Similarity	NPD5779	Approved
0.6436	Remote Similarity	NPD5778	Approved
0.6435	Remote Similarity	NPD7100	Approved
0.6435	Remote Similarity	NPD7101	Approved
0.6429	Remote Similarity	NPD4632	Approved
0.6404	Remote Similarity	NPD6317	Approved
0.6404	Remote Similarity	NPD5777	Approved
0.6395	Remote Similarity	NPD4224	Phase 2
0.6392	Remote Similarity	NPD5329	Approved
0.6387	Remote Similarity	NPD7507	Approved
0.6379	Remote Similarity	NPD6319	Approved
0.6373	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6314	Approved
0.6348	Remote Similarity	NPD6335	Approved
0.6348	Remote Similarity	NPD6313	Approved
0.6344	Remote Similarity	NPD3617	Approved
0.6339	Remote Similarity	NPD6053	Discontinued
0.6337	Remote Similarity	NPD7637	Suspended
0.633	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5205	Approved
0.6327	Remote Similarity	NPD5279	Phase 3
0.6327	Remote Similarity	NPD4693	Phase 3
0.6327	Remote Similarity	NPD4690	Approved
0.6327	Remote Similarity	NPD5690	Phase 2
0.6327	Remote Similarity	NPD4688	Approved
0.6327	Remote Similarity	NPD4138	Approved
0.6327	Remote Similarity	NPD4689	Approved
0.6316	Remote Similarity	NPD6868	Approved
0.6306	Remote Similarity	NPD6371	Approved
0.6303	Remote Similarity	NPD7492	Approved
0.63	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7645	Phase 2
0.6273	Remote Similarity	NPD4729	Approved
0.6273	Remote Similarity	NPD4730	Approved
0.6273	Remote Similarity	NPD5128	Approved
0.6261	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD6616	Approved
0.6239	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD6054	Approved
0.6239	Remote Similarity	NPD4767	Approved
0.6238	Remote Similarity	NPD46	Approved
0.6238	Remote Similarity	NPD6698	Approved
0.6238	Remote Similarity	NPD5692	Phase 3
0.623	Remote Similarity	NPD7319	Approved
0.6222	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7525	Registered
0.6204	Remote Similarity	NPD4754	Approved
0.6198	Remote Similarity	NPD7078	Approved
0.6196	Remote Similarity	NPD8039	Approved
0.6196	Remote Similarity	NPD3703	Phase 2
0.6186	Remote Similarity	NPD6015	Approved
0.6186	Remote Similarity	NPD7154	Phase 3
0.6186	Remote Similarity	NPD6908	Approved
0.6186	Remote Similarity	NPD6695	Phase 3
0.6186	Remote Similarity	NPD6016	Approved
0.6186	Remote Similarity	NPD6909	Approved
0.6186	Remote Similarity	NPD6921	Approved
0.6186	Remote Similarity	NPD5983	Phase 2
0.6182	Remote Similarity	NPD6412	Phase 2
0.618	Remote Similarity	NPD3698	Phase 2

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