NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.17
Volume:	280.721
LogP:	2.487
LogD:	2.267
LogS:	-3.188
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	4.792
Fsp3:	0.812
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:	-4.717
MDCK Permeability:	2.588514871604275e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.188
Plasma Protein Binding (PPB):	68.94763946533203%
Volume Distribution (VD):	0.834
Pgp-substrate:	38.86639404296875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.138
CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.218
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.23
CYP2C9-substrate:	0.112
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.626
CYP3A4-substrate:	0.348

ADMET: Excretion

Clearance (CL):	9.377
Half-life (T1/2):	0.481

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.36
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.715
Maximum Recommended Daily Dose:	0.857
Skin Sensitization:	0.921
Carcinogencity:	0.871
Eye Corrosion:	0.848
Eye Irritation:	0.817
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC470012

Natural Product ID:	NPC470012
*Common Name:**	Carabrol
IUPAC Name:	(3aR,4aS,5S,5aR,6aR)-5-[(3S)-3-hydroxybutyl]-4a,5a-dimethyl-3-methylidene-4,5,6,6a-tetrahydro-3aH-cyclopropa[f][1]benzofuran-2-one
Synonyms:	Carabrol
Standard InCHIKey:	FDFBRCKWUMZDTG-AYWPFRTFSA-N
Standard InCHI:	InChI=1S/C16H24O3/c1-9(17)5-6-13-15(3)7-11-10(2)14(18)19-12(11)8-16(13,15)4/h9,11-13,17H,2,5-8H2,1,3-4H3/t9-,11+,12+,13-,15-,16+/m0/s1
SMILES:	C[C@@H](CC[C@@H]1[C@@]2([C@@]1(C)C[C@H]1[C@@H](C2)OC(=O)C1=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644101
PubChem CID:	53323204
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:0000502] Xanthanolides

*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
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	whole plant	Changshou County, Chongqing, China	2008-Aug	PMID[21109433]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26316467]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26394911]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23499	Carpesium faberi	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
IC50	17

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11.4	ug.mL-1	PMID[558911]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	47000.0	nM	PMID[558913]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	4700.0	nM	PMID[558913]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	6600.0	nM	PMID[558913]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	2600.0	nM	PMID[558913]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	940.0	nM	PMID[558913]
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	=	4000.0	nM	PMID[558913]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[558913]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	8900.0	nM	PMID[558913]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	360.0	nM	PMID[558913]
NPT2637	Organism	Colletotrichum lagenarium	Colletotrichum lagenarium	IC50	=	24.81	ug.mL-1	PMID[558912]
NPT2637	Organism	Colletotrichum lagenarium	Colletotrichum lagenarium	IC50	=	20.14	ug.mL-1	PMID[558912]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[558913]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	45500.0	nM	PMID[558913]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	>	100000.0	nM	PMID[558913]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	>	128.0	ug.mL-1	PMID[558914]

☑ 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 NPC470012 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	182
0.1-0.2	1395
0.2-0.3	5425
0.3-0.4	13950
0.4-0.5	8201
0.5-0.6	6682
0.6-0.7	5618
0.7-0.8	1182
0.8-0.85	45
0.85-0.9	12
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC477920
0.939	High Similarity	NPC219011
0.939	High Similarity	NPC470011
0.9286	High Similarity	NPC181103
0.9286	High Similarity	NPC305029
0.9268	High Similarity	NPC194637
0.9167	High Similarity	NPC85698
0.907	High Similarity	NPC116620
0.8941	High Similarity	NPC185638
0.8941	High Similarity	NPC9231
0.8916	High Similarity	NPC226988
0.8901	High Similarity	NPC473155
0.8864	High Similarity	NPC233345
0.8864	High Similarity	NPC186363
0.8795	High Similarity	NPC38642
0.8778	High Similarity	NPC259042
0.8778	High Similarity	NPC157686
0.8736	High Similarity	NPC277771
0.8681	High Similarity	NPC284518
0.8667	High Similarity	NPC148000
0.8667	High Similarity	NPC469596
0.8667	High Similarity	NPC24861
0.8667	High Similarity	NPC225474
0.8621	High Similarity	NPC175293
0.8602	High Similarity	NPC476303
0.8587	High Similarity	NPC136781
0.8587	High Similarity	NPC473963
0.8571	High Similarity	NPC183012
0.8571	High Similarity	NPC209318
0.8571	High Similarity	NPC223330
0.8526	High Similarity	NPC476237
0.8488	Intermediate Similarity	NPC97505
0.8478	Intermediate Similarity	NPC93245
0.8478	Intermediate Similarity	NPC473964
0.8404	Intermediate Similarity	NPC47024
0.837	Intermediate Similarity	NPC90014
0.8333	Intermediate Similarity	NPC176883
0.8333	Intermediate Similarity	NPC158488
0.8333	Intermediate Similarity	NPC475776
0.8333	Intermediate Similarity	NPC263951
0.8316	Intermediate Similarity	NPC475958
0.8316	Intermediate Similarity	NPC308824
0.8315	Intermediate Similarity	NPC477302
0.8298	Intermediate Similarity	NPC476806
0.8298	Intermediate Similarity	NPC216478
0.8298	Intermediate Similarity	NPC476807
0.8295	Intermediate Similarity	NPC250981
0.8295	Intermediate Similarity	NPC6979
0.828	Intermediate Similarity	NPC307164
0.828	Intermediate Similarity	NPC228766
0.828	Intermediate Similarity	NPC165528
0.8242	Intermediate Similarity	NPC72845
0.8229	Intermediate Similarity	NPC164551
0.8222	Intermediate Similarity	NPC50488
0.8222	Intermediate Similarity	NPC218927
0.8222	Intermediate Similarity	NPC206001
0.8222	Intermediate Similarity	NPC194642
0.8222	Intermediate Similarity	NPC288699
0.8222	Intermediate Similarity	NPC73995
0.8222	Intermediate Similarity	NPC474396
0.8193	Intermediate Similarity	NPC92489
0.8191	Intermediate Similarity	NPC474395
0.8191	Intermediate Similarity	NPC474343
0.8161	Intermediate Similarity	NPC470948
0.8152	Intermediate Similarity	NPC139692
0.8144	Intermediate Similarity	NPC61442
0.8144	Intermediate Similarity	NPC156681
0.8132	Intermediate Similarity	NPC153853
0.8132	Intermediate Similarity	NPC152467
0.8125	Intermediate Similarity	NPC242666
0.8111	Intermediate Similarity	NPC136879
0.8111	Intermediate Similarity	NPC215831
0.8105	Intermediate Similarity	NPC252295
0.809	Intermediate Similarity	NPC329692
0.8065	Intermediate Similarity	NPC474841
0.8065	Intermediate Similarity	NPC471446
0.8065	Intermediate Similarity	NPC473434
0.8065	Intermediate Similarity	NPC250075
0.8065	Intermediate Similarity	NPC57117
0.8046	Intermediate Similarity	NPC123880
0.8046	Intermediate Similarity	NPC471159
0.8046	Intermediate Similarity	NPC178676
0.8043	Intermediate Similarity	NPC49420
0.8022	Intermediate Similarity	NPC168131
0.8021	Intermediate Similarity	NPC474012
0.8021	Intermediate Similarity	NPC476299
0.8021	Intermediate Similarity	NPC470906
0.8	Intermediate Similarity	NPC474921
0.8	Intermediate Similarity	NPC312561
0.7979	Intermediate Similarity	NPC56369
0.7979	Intermediate Similarity	NPC210214
0.7978	Intermediate Similarity	NPC52628
0.7976	Intermediate Similarity	NPC476601
0.7957	Intermediate Similarity	NPC147272
0.7957	Intermediate Similarity	NPC294263
0.7955	Intermediate Similarity	NPC243347
0.7938	Intermediate Similarity	NPC111292
0.7935	Intermediate Similarity	NPC469368
0.7931	Intermediate Similarity	NPC475951
0.7931	Intermediate Similarity	NPC473420
0.7912	Intermediate Similarity	NPC477128
0.7912	Intermediate Similarity	NPC473229
0.79	Intermediate Similarity	NPC78966
0.79	Intermediate Similarity	NPC284732
0.79	Intermediate Similarity	NPC110496
0.7895	Intermediate Similarity	NPC104568
0.7895	Intermediate Similarity	NPC154526
0.7895	Intermediate Similarity	NPC472362
0.7895	Intermediate Similarity	NPC134072
0.7895	Intermediate Similarity	NPC13949
0.7895	Intermediate Similarity	NPC234993
0.7895	Intermediate Similarity	NPC242848
0.7895	Intermediate Similarity	NPC472363
0.7882	Intermediate Similarity	NPC474433
0.7872	Intermediate Similarity	NPC471720
0.7872	Intermediate Similarity	NPC477130
0.7872	Intermediate Similarity	NPC477129
0.7865	Intermediate Similarity	NPC159635
0.7865	Intermediate Similarity	NPC130966
0.7857	Intermediate Similarity	NPC476081
0.7857	Intermediate Similarity	NPC469606
0.7857	Intermediate Similarity	NPC273005
0.7857	Intermediate Similarity	NPC31058
0.7849	Intermediate Similarity	NPC250753
0.7835	Intermediate Similarity	NPC201406
0.7826	Intermediate Similarity	NPC253618
0.7826	Intermediate Similarity	NPC5509
0.7826	Intermediate Similarity	NPC128496
0.7826	Intermediate Similarity	NPC77001
0.7822	Intermediate Similarity	NPC189075
0.7822	Intermediate Similarity	NPC275539
0.7822	Intermediate Similarity	NPC37628
0.7812	Intermediate Similarity	NPC121402
0.7812	Intermediate Similarity	NPC175351
0.7812	Intermediate Similarity	NPC132753
0.7812	Intermediate Similarity	NPC224356
0.7812	Intermediate Similarity	NPC73911
0.7812	Intermediate Similarity	NPC151681
0.7802	Intermediate Similarity	NPC476932
0.78	Intermediate Similarity	NPC469607
0.7789	Intermediate Similarity	NPC98639
0.7778	Intermediate Similarity	NPC120321
0.7778	Intermediate Similarity	NPC99510
0.7778	Intermediate Similarity	NPC470310
0.7778	Intermediate Similarity	NPC476602
0.7778	Intermediate Similarity	NPC76518
0.7778	Intermediate Similarity	NPC110405
0.7778	Intermediate Similarity	NPC36688
0.7778	Intermediate Similarity	NPC86316
0.7778	Intermediate Similarity	NPC72842
0.7778	Intermediate Similarity	NPC106416
0.7766	Intermediate Similarity	NPC166346
0.7766	Intermediate Similarity	NPC474436
0.7766	Intermediate Similarity	NPC199543
0.7766	Intermediate Similarity	NPC115021
0.7766	Intermediate Similarity	NPC49776
0.7766	Intermediate Similarity	NPC63118
0.7766	Intermediate Similarity	NPC470224
0.7755	Intermediate Similarity	NPC471412
0.7755	Intermediate Similarity	NPC81530
0.7755	Intermediate Similarity	NPC303559
0.7753	Intermediate Similarity	NPC22611
0.7753	Intermediate Similarity	NPC471037
0.7745	Intermediate Similarity	NPC474243
0.7742	Intermediate Similarity	NPC281942
0.7742	Intermediate Similarity	NPC232426
0.7742	Intermediate Similarity	NPC310479
0.7732	Intermediate Similarity	NPC473154
0.7732	Intermediate Similarity	NPC16911
0.7732	Intermediate Similarity	NPC57079
0.7732	Intermediate Similarity	NPC478056
0.7732	Intermediate Similarity	NPC124703
0.7732	Intermediate Similarity	NPC108368
0.7732	Intermediate Similarity	NPC316598
0.7732	Intermediate Similarity	NPC23364
0.7732	Intermediate Similarity	NPC78427
0.7732	Intermediate Similarity	NPC234617
0.7732	Intermediate Similarity	NPC98868
0.7732	Intermediate Similarity	NPC124512
0.7732	Intermediate Similarity	NPC278386
0.7732	Intermediate Similarity	NPC159763
0.7723	Intermediate Similarity	NPC470952
0.7717	Intermediate Similarity	NPC146937
0.7717	Intermediate Similarity	NPC226863
0.7708	Intermediate Similarity	NPC200054
0.7708	Intermediate Similarity	NPC29410
0.7708	Intermediate Similarity	NPC256227
0.7701	Intermediate Similarity	NPC470244
0.7701	Intermediate Similarity	NPC470239
0.77	Intermediate Similarity	NPC283850
0.7692	Intermediate Similarity	NPC56593
0.7692	Intermediate Similarity	NPC472505
0.7692	Intermediate Similarity	NPC325594
0.7692	Intermediate Similarity	NPC12774
0.7692	Intermediate Similarity	NPC473226
0.7684	Intermediate Similarity	NPC47853
0.7684	Intermediate Similarity	NPC66581
0.7684	Intermediate Similarity	NPC470697
0.7677	Intermediate Similarity	NPC32577
0.7677	Intermediate Similarity	NPC155332

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 NPC470012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1936
0.2-0.3	3894
0.3-0.4	2138
0.4-0.5	577
0.5-0.6	238
0.6-0.7	178
0.7-0.8	10
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
0.7732	Intermediate Similarity	NPD4225	Approved
0.7582	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1694	Approved
0.7474	Intermediate Similarity	NPD8034	Phase 2
0.7474	Intermediate Similarity	NPD8035	Phase 2
0.7374	Intermediate Similarity	NPD7638	Approved
0.7312	Intermediate Similarity	NPD3618	Phase 1
0.73	Intermediate Similarity	NPD7639	Approved
0.73	Intermediate Similarity	NPD7640	Approved
0.7253	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7115	Discovery
0.7216	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD7748	Approved
0.7113	Intermediate Similarity	NPD7515	Phase 2
0.71	Intermediate Similarity	NPD7902	Approved
0.7071	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3667	Approved
0.6939	Remote Similarity	NPD6079	Approved
0.6916	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4786	Approved
0.6907	Remote Similarity	NPD5328	Approved
0.69	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5697	Approved
0.6852	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5785	Approved
0.6827	Remote Similarity	NPD7632	Discontinued
0.6822	Remote Similarity	NPD6011	Approved
0.6822	Remote Similarity	NPD6899	Approved
0.6822	Remote Similarity	NPD6881	Approved
0.6809	Remote Similarity	NPD4788	Approved
0.68	Remote Similarity	NPD7900	Approved
0.68	Remote Similarity	NPD6001	Approved
0.68	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6402	Approved
0.6792	Remote Similarity	NPD5739	Approved
0.6792	Remote Similarity	NPD6675	Approved
0.6792	Remote Similarity	NPD6008	Approved
0.6792	Remote Similarity	NPD7128	Approved
0.6789	Remote Similarity	NPD6649	Approved
0.6789	Remote Similarity	NPD6650	Approved
0.6778	Remote Similarity	NPD6117	Approved
0.6771	Remote Similarity	NPD7146	Approved
0.6771	Remote Similarity	NPD6684	Approved
0.6771	Remote Similarity	NPD5330	Approved
0.6771	Remote Similarity	NPD7334	Approved
0.6771	Remote Similarity	NPD6409	Approved
0.6771	Remote Similarity	NPD7521	Approved
0.6759	Remote Similarity	NPD6014	Approved
0.6759	Remote Similarity	NPD6372	Approved
0.6759	Remote Similarity	NPD6013	Approved
0.6759	Remote Similarity	NPD6373	Approved
0.6759	Remote Similarity	NPD6012	Approved
0.6742	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3133	Approved
0.6737	Remote Similarity	NPD3665	Phase 1
0.6737	Remote Similarity	NPD3666	Approved
0.6729	Remote Similarity	NPD5701	Approved
0.6703	Remote Similarity	NPD6116	Phase 1
0.6701	Remote Similarity	NPD3573	Approved
0.67	Remote Similarity	NPD4202	Approved
0.6697	Remote Similarity	NPD6883	Approved
0.6697	Remote Similarity	NPD7290	Approved
0.6697	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD8130	Phase 1
0.6636	Remote Similarity	NPD6869	Approved
0.6636	Remote Similarity	NPD6617	Approved
0.6636	Remote Similarity	NPD6847	Approved
0.6633	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6903	Approved
0.663	Remote Similarity	NPD6118	Approved
0.663	Remote Similarity	NPD6697	Approved
0.663	Remote Similarity	NPD6115	Approved
0.663	Remote Similarity	NPD6114	Approved
0.6602	Remote Similarity	NPD6084	Phase 2
0.6602	Remote Similarity	NPD5173	Approved
0.6602	Remote Similarity	NPD6083	Phase 2
0.66	Remote Similarity	NPD6411	Approved
0.6577	Remote Similarity	NPD8297	Approved
0.6577	Remote Similarity	NPD6882	Approved
0.6574	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5695	Phase 3
0.6566	Remote Similarity	NPD1695	Approved
0.6545	Remote Similarity	NPD6371	Approved
0.6538	Remote Similarity	NPD5696	Approved
0.6518	Remote Similarity	NPD8133	Approved
0.6509	Remote Similarity	NPD5211	Phase 2
0.65	Remote Similarity	NPD46	Approved
0.65	Remote Similarity	NPD6698	Approved
0.6495	Remote Similarity	NPD1696	Phase 3
0.6495	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5286	Approved
0.6476	Remote Similarity	NPD5285	Approved
0.6476	Remote Similarity	NPD4696	Approved
0.6465	Remote Similarity	NPD6672	Approved
0.6465	Remote Similarity	NPD5737	Approved
0.6442	Remote Similarity	NPD4755	Approved
0.6436	Remote Similarity	NPD5693	Phase 1
0.6429	Remote Similarity	NPD5279	Phase 3
0.6429	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5223	Approved
0.6415	Remote Similarity	NPD5344	Discontinued
0.641	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6274	Approved
0.6404	Remote Similarity	NPD6868	Approved
0.64	Remote Similarity	NPD6101	Approved
0.64	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3668	Phase 3
0.6389	Remote Similarity	NPD5141	Approved
0.6373	Remote Similarity	NPD5778	Approved
0.6373	Remote Similarity	NPD5779	Approved
0.6372	Remote Similarity	NPD4632	Approved
0.6355	Remote Similarity	NPD5224	Approved
0.6355	Remote Similarity	NPD5226	Approved
0.6355	Remote Similarity	NPD5225	Approved
0.6355	Remote Similarity	NPD4633	Approved
0.6354	Remote Similarity	NPD5209	Approved
0.6348	Remote Similarity	NPD6317	Approved
0.6337	Remote Similarity	NPD5207	Approved
0.6333	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5363	Approved
0.6321	Remote Similarity	NPD4700	Approved
0.6316	Remote Similarity	NPD4695	Discontinued
0.6304	Remote Similarity	NPD3703	Phase 2
0.6304	Remote Similarity	NPD3702	Approved
0.6304	Remote Similarity	NPD8039	Approved
0.6303	Remote Similarity	NPD7604	Phase 2
0.6296	Remote Similarity	NPD5174	Approved
0.6296	Remote Similarity	NPD5175	Approved
0.6293	Remote Similarity	NPD6314	Approved
0.6293	Remote Similarity	NPD6313	Approved
0.6293	Remote Similarity	NPD6335	Approved
0.6289	Remote Similarity	NPD7154	Phase 3
0.6289	Remote Similarity	NPD5362	Discontinued
0.6277	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5284	Approved
0.6275	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD4629	Approved
0.6239	Remote Similarity	NPD7101	Approved
0.6239	Remote Similarity	NPD7100	Approved
0.6238	Remote Similarity	NPD4753	Phase 2
0.6237	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7645	Phase 2
0.6207	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6009	Approved
0.6198	Remote Similarity	NPD7507	Approved
0.6186	Remote Similarity	NPD6319	Approved
0.6186	Remote Similarity	NPD4221	Approved
0.6186	Remote Similarity	NPD4269	Approved
0.6186	Remote Similarity	NPD4223	Phase 3
0.6186	Remote Similarity	NPD4270	Approved
0.6168	Remote Similarity	NPD6648	Approved
0.6162	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5282	Discontinued
0.6154	Remote Similarity	NPD5777	Approved
0.6147	Remote Similarity	NPD4754	Approved
0.6146	Remote Similarity	NPD7525	Registered
0.614	Remote Similarity	NPD6053	Discontinued
0.6139	Remote Similarity	NPD5208	Approved
0.6136	Remote Similarity	NPD4224	Phase 2
0.6134	Remote Similarity	NPD5983	Phase 2
0.6129	Remote Similarity	NPD6942	Approved
0.6129	Remote Similarity	NPD7339	Approved
0.6126	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7637	Suspended
0.6116	Remote Similarity	NPD7492	Approved
0.6111	Remote Similarity	NPD3698	Phase 2
0.6105	Remote Similarity	NPD3617	Approved
0.61	Remote Similarity	NPD4519	Discontinued
0.61	Remote Similarity	NPD5690	Phase 2
0.61	Remote Similarity	NPD4623	Approved
0.61	Remote Similarity	NPD5786	Approved
0.61	Remote Similarity	NPD6098	Approved
0.6078	Remote Similarity	NPD6080	Approved
0.6078	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6904	Approved
0.6078	Remote Similarity	NPD6673	Approved
0.6078	Remote Similarity	NPD6051	Approved
0.6071	Remote Similarity	NPD4730	Approved
0.6071	Remote Similarity	NPD5168	Approved
0.6071	Remote Similarity	NPD5128	Approved
0.6071	Remote Similarity	NPD4729	Approved
0.6066	Remote Similarity	NPD6616	Approved
0.6061	Remote Similarity	NPD4197	Approved
0.6061	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6054	Approved
0.6048	Remote Similarity	NPD7319	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