NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.15
Volume:	286.925
LogP:	1.119
LogD:	0.313
LogS:	-1.844
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	5.371
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.653
MDCK Permeability:	1.1997219189652242e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.201
20% Bioavailability (F20%):	0.611
30% Bioavailability (F30%):	0.753

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.709
Plasma Protein Binding (PPB):	51.670440673828125%
Volume Distribution (VD):	0.404
Pgp-substrate:	37.57893371582031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.807
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.465
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	3.095
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.835
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.59
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.92
Carcinogencity:	0.447
Eye Corrosion:	0.011
Eye Irritation:	0.528
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC120446

Natural Product ID:	NPC120446
*Common Name:**	Dihydrophaseic Acid
IUPAC Name:	(2Z,4E)-5-[(1R,3S,5R,8S)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid
Synonyms:
Standard InCHIKey:	XIVFQYWMMJWUCD-VSTJRZLJSA-N
Standard InCHI:	InChI=1S/C15H22O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,11,16,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-/t11-,13+,14+,15-/m0/s1
SMILES:	C/C(=C/C(=O)O)/C=C/[C@@]1([C@]2(C)C[C@@H](C[C@@]1(C)OC2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594246
PubChem CID:	11988272
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002245] Abscisic acids 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
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[26110443]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17612	Xanthium sibiricum	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	3

Activity Type	# Activity
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[494791]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	>	35000.0	nM	PMID[494791]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	35000.0	nM	PMID[494791]

☑ 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 NPC120446 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	176
0.1-0.2	1023
0.2-0.3	3906
0.3-0.4	6484
0.4-0.5	15070
0.5-0.6	9078
0.6-0.7	5650
0.7-0.8	1277
0.8-0.85	31
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8586	High Similarity	NPC11956
0.85	High Similarity	NPC23584
0.8469	Intermediate Similarity	NPC475068
0.8384	Intermediate Similarity	NPC38855
0.83	Intermediate Similarity	NPC472554
0.8229	Intermediate Similarity	NPC473675
0.8222	Intermediate Similarity	NPC236707
0.8218	Intermediate Similarity	NPC472552
0.8208	Intermediate Similarity	NPC328074
0.8208	Intermediate Similarity	NPC321272
0.8208	Intermediate Similarity	NPC317460
0.8208	Intermediate Similarity	NPC470025
0.819	Intermediate Similarity	NPC177047
0.8182	Intermediate Similarity	NPC205143
0.8173	Intermediate Similarity	NPC38948
0.8173	Intermediate Similarity	NPC181994
0.8173	Intermediate Similarity	NPC50124
0.8172	Intermediate Similarity	NPC471267
0.8172	Intermediate Similarity	NPC298595
0.8155	Intermediate Similarity	NPC471206
0.8152	Intermediate Similarity	NPC471987
0.8144	Intermediate Similarity	NPC110022
0.8132	Intermediate Similarity	NPC471270
0.8131	Intermediate Similarity	NPC470027
0.8113	Intermediate Similarity	NPC17791
0.81	Intermediate Similarity	NPC278008
0.8095	Intermediate Similarity	NPC206618
0.8081	Intermediate Similarity	NPC473153
0.8081	Intermediate Similarity	NPC472995
0.8081	Intermediate Similarity	NPC165632
0.8077	Intermediate Similarity	NPC471205
0.8061	Intermediate Similarity	NPC469491
0.8037	Intermediate Similarity	NPC472002
0.8022	Intermediate Similarity	NPC95124
0.8022	Intermediate Similarity	NPC471266
0.802	Intermediate Similarity	NPC475877
0.802	Intermediate Similarity	NPC188968
0.802	Intermediate Similarity	NPC272223
0.8019	Intermediate Similarity	NPC316708
0.8018	Intermediate Similarity	NPC475885
0.798	Intermediate Similarity	NPC86893
0.798	Intermediate Similarity	NPC276110
0.798	Intermediate Similarity	NPC292178
0.7961	Intermediate Similarity	NPC474575
0.7961	Intermediate Similarity	NPC474822
0.7959	Intermediate Similarity	NPC53555
0.7944	Intermediate Similarity	NPC188738
0.7944	Intermediate Similarity	NPC470026
0.7941	Intermediate Similarity	NPC11974
0.7928	Intermediate Similarity	NPC156745
0.7928	Intermediate Similarity	NPC236918
0.7925	Intermediate Similarity	NPC475586
0.7925	Intermediate Similarity	NPC316974
0.7921	Intermediate Similarity	NPC278673
0.7905	Intermediate Similarity	NPC122816
0.7905	Intermediate Similarity	NPC67321
0.7905	Intermediate Similarity	NPC187435
0.79	Intermediate Similarity	NPC57664
0.789	Intermediate Similarity	NPC472400
0.789	Intermediate Similarity	NPC73314
0.7885	Intermediate Similarity	NPC473068
0.7879	Intermediate Similarity	NPC105490
0.7876	Intermediate Similarity	NPC196130
0.7864	Intermediate Similarity	NPC470972
0.7864	Intermediate Similarity	NPC214277
0.7864	Intermediate Similarity	NPC165578
0.7864	Intermediate Similarity	NPC470571
0.7864	Intermediate Similarity	NPC472815
0.7864	Intermediate Similarity	NPC150463
0.7857	Intermediate Similarity	NPC472759
0.7857	Intermediate Similarity	NPC329080
0.7857	Intermediate Similarity	NPC475003
0.7843	Intermediate Similarity	NPC16601
0.7838	Intermediate Similarity	NPC284707
0.7835	Intermediate Similarity	NPC115607
0.783	Intermediate Similarity	NPC48548
0.783	Intermediate Similarity	NPC470024
0.783	Intermediate Similarity	NPC217921
0.783	Intermediate Similarity	NPC128795
0.783	Intermediate Similarity	NPC311223
0.783	Intermediate Similarity	NPC135015
0.7822	Intermediate Similarity	NPC473244
0.7822	Intermediate Similarity	NPC199099
0.7822	Intermediate Similarity	NPC254121
0.7822	Intermediate Similarity	NPC472998
0.7818	Intermediate Similarity	NPC179626
0.7812	Intermediate Similarity	NPC44538
0.781	Intermediate Similarity	NPC51719
0.78	Intermediate Similarity	NPC476720
0.7798	Intermediate Similarity	NPC469463
0.7798	Intermediate Similarity	NPC474271
0.7798	Intermediate Similarity	NPC469454
0.7798	Intermediate Similarity	NPC472757
0.7798	Intermediate Similarity	NPC469496
0.7789	Intermediate Similarity	NPC196911
0.7789	Intermediate Similarity	NPC471379
0.7788	Intermediate Similarity	NPC233500
0.7788	Intermediate Similarity	NPC473070
0.7788	Intermediate Similarity	NPC45897
0.7778	Intermediate Similarity	NPC247031
0.7778	Intermediate Similarity	NPC304180
0.7778	Intermediate Similarity	NPC162615
0.7778	Intermediate Similarity	NPC100329
0.7778	Intermediate Similarity	NPC152778
0.7778	Intermediate Similarity	NPC7349
0.7778	Intermediate Similarity	NPC205034
0.7778	Intermediate Similarity	NPC97939
0.7778	Intermediate Similarity	NPC132790
0.7778	Intermediate Similarity	NPC179798
0.7767	Intermediate Similarity	NPC96784
0.7767	Intermediate Similarity	NPC475617
0.7767	Intermediate Similarity	NPC235920
0.7757	Intermediate Similarity	NPC40728
0.7755	Intermediate Similarity	NPC312471
0.7755	Intermediate Similarity	NPC191323
0.7755	Intermediate Similarity	NPC471378
0.7755	Intermediate Similarity	NPC153853
0.7748	Intermediate Similarity	NPC53396
0.7748	Intermediate Similarity	NPC98249
0.7748	Intermediate Similarity	NPC156252
0.7748	Intermediate Similarity	NPC469684
0.7745	Intermediate Similarity	NPC124512
0.7745	Intermediate Similarity	NPC159763
0.7745	Intermediate Similarity	NPC278386
0.7736	Intermediate Similarity	NPC109376
0.7736	Intermediate Similarity	NPC125423
0.7736	Intermediate Similarity	NPC475074
0.7736	Intermediate Similarity	NPC88013
0.7732	Intermediate Similarity	NPC470260
0.7732	Intermediate Similarity	NPC75443
0.7723	Intermediate Similarity	NPC284194
0.7723	Intermediate Similarity	NPC471765
0.7723	Intermediate Similarity	NPC103165
0.7723	Intermediate Similarity	NPC210717
0.7723	Intermediate Similarity	NPC211810
0.7723	Intermediate Similarity	NPC221801
0.7723	Intermediate Similarity	NPC471903
0.7719	Intermediate Similarity	NPC471082
0.7714	Intermediate Similarity	NPC194941
0.7714	Intermediate Similarity	NPC152966
0.7714	Intermediate Similarity	NPC473543
0.7714	Intermediate Similarity	NPC296950
0.7708	Intermediate Similarity	NPC175145
0.7708	Intermediate Similarity	NPC475684
0.7708	Intermediate Similarity	NPC472379
0.7708	Intermediate Similarity	NPC475069
0.7708	Intermediate Similarity	NPC61527
0.77	Intermediate Similarity	NPC57117
0.7692	Intermediate Similarity	NPC109195
0.7692	Intermediate Similarity	NPC475038
0.7685	Intermediate Similarity	NPC478211
0.7685	Intermediate Similarity	NPC119550
0.7685	Intermediate Similarity	NPC5103
0.7684	Intermediate Similarity	NPC102048
0.7679	Intermediate Similarity	NPC124676
0.7679	Intermediate Similarity	NPC478206
0.7679	Intermediate Similarity	NPC478205
0.7679	Intermediate Similarity	NPC146280
0.7679	Intermediate Similarity	NPC108581
0.7677	Intermediate Similarity	NPC78594
0.7677	Intermediate Similarity	NPC91251
0.767	Intermediate Similarity	NPC474571
0.767	Intermediate Similarity	NPC254567
0.767	Intermediate Similarity	NPC324841
0.767	Intermediate Similarity	NPC79303
0.7664	Intermediate Similarity	NPC102843
0.7664	Intermediate Similarity	NPC306265
0.7664	Intermediate Similarity	NPC224660
0.7664	Intermediate Similarity	NPC472218
0.7664	Intermediate Similarity	NPC472219
0.7664	Intermediate Similarity	NPC473069
0.7664	Intermediate Similarity	NPC472217
0.766	Intermediate Similarity	NPC259858
0.7658	Intermediate Similarity	NPC234858
0.7658	Intermediate Similarity	NPC471127
0.7658	Intermediate Similarity	NPC154363
0.7653	Intermediate Similarity	NPC170633
0.7653	Intermediate Similarity	NPC161560
0.7653	Intermediate Similarity	NPC16265
0.7653	Intermediate Similarity	NPC291875
0.7653	Intermediate Similarity	NPC246028
0.7653	Intermediate Similarity	NPC97103
0.7653	Intermediate Similarity	NPC314727
0.7653	Intermediate Similarity	NPC82876
0.7647	Intermediate Similarity	NPC99726
0.7642	Intermediate Similarity	NPC82251
0.7642	Intermediate Similarity	NPC239961
0.7642	Intermediate Similarity	NPC477125
0.7642	Intermediate Similarity	NPC172867
0.7642	Intermediate Similarity	NPC470980
0.7642	Intermediate Similarity	NPC218158
0.7636	Intermediate Similarity	NPC475966
0.7636	Intermediate Similarity	NPC56448
0.7636	Intermediate Similarity	NPC478212
0.7629	Intermediate Similarity	NPC245004
0.7629	Intermediate Similarity	NPC473891
0.7624	Intermediate Similarity	NPC469583
0.7624	Intermediate Similarity	NPC111273
0.7624	Intermediate Similarity	NPC471915
0.7619	Intermediate Similarity	NPC474124

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 NPC120446 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1240
0.2-0.3	3710
0.3-0.4	2587
0.4-0.5	1003
0.5-0.6	298
0.6-0.7	151
0.7-0.8	13
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
0.83	Intermediate Similarity	NPD5344	Discontinued
0.82	Intermediate Similarity	NPD6648	Approved
0.7745	Intermediate Similarity	NPD4225	Approved
0.7449	Intermediate Similarity	NPD7524	Approved
0.7431	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7516	Approved
0.7228	Intermediate Similarity	NPD7838	Discovery
0.7217	Intermediate Similarity	NPD7327	Approved
0.7217	Intermediate Similarity	NPD7328	Approved
0.717	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD7639	Approved
0.7157	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7638	Approved
0.7054	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6695	Phase 3
0.7034	Intermediate Similarity	NPD7503	Approved
0.6891	Remote Similarity	NPD8379	Approved
0.6891	Remote Similarity	NPD8335	Approved
0.6891	Remote Similarity	NPD8296	Approved
0.6891	Remote Similarity	NPD8380	Approved
0.6891	Remote Similarity	NPD8033	Approved
0.6891	Remote Similarity	NPD8378	Approved
0.6875	Remote Similarity	NPD6686	Approved
0.6838	Remote Similarity	NPD7115	Discovery
0.6827	Remote Similarity	NPD7983	Approved
0.6807	Remote Similarity	NPD8377	Approved
0.6807	Remote Similarity	NPD8294	Approved
0.6786	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7750	Discontinued
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.6759	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7332	Phase 2
0.6735	Remote Similarity	NPD7514	Phase 3
0.6735	Remote Similarity	NPD6930	Phase 2
0.6735	Remote Similarity	NPD6931	Approved
0.6731	Remote Similarity	NPD6698	Approved
0.6731	Remote Similarity	NPD46	Approved
0.6731	Remote Similarity	NPD3168	Discontinued
0.6726	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6633	Remote Similarity	NPD6929	Approved
0.6609	Remote Similarity	NPD6371	Approved
0.6577	Remote Similarity	NPD7632	Discontinued
0.6532	Remote Similarity	NPD7507	Approved
0.6531	Remote Similarity	NPD7145	Approved
0.6509	Remote Similarity	NPD7087	Discontinued
0.6508	Remote Similarity	NPD7319	Approved
0.6505	Remote Similarity	NPD4249	Approved
0.65	Remote Similarity	NPD6902	Approved
0.6496	Remote Similarity	NPD8297	Approved
0.6491	Remote Similarity	NPD5697	Approved
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD8515	Approved
0.6471	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7492	Approved
0.6442	Remote Similarity	NPD4251	Approved
0.6442	Remote Similarity	NPD4250	Approved
0.6435	Remote Similarity	NPD6899	Approved
0.6435	Remote Similarity	NPD6881	Approved
0.6429	Remote Similarity	NPD6932	Approved
0.6429	Remote Similarity	NPD5776	Phase 2
0.6429	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6925	Approved
0.6417	Remote Similarity	NPD6009	Approved
0.6408	Remote Similarity	NPD6893	Approved
0.6408	Remote Similarity	NPD1696	Phase 3
0.6404	Remote Similarity	NPD6402	Approved
0.6404	Remote Similarity	NPD7128	Approved
0.6404	Remote Similarity	NPD5739	Approved
0.6404	Remote Similarity	NPD6675	Approved
0.6404	Remote Similarity	NPD6008	Approved
0.64	Remote Similarity	NPD6616	Approved
0.6393	Remote Similarity	NPD6054	Approved
0.6392	Remote Similarity	NPD8264	Approved
0.6389	Remote Similarity	NPD5282	Discontinued
0.6379	Remote Similarity	NPD6014	Approved
0.6379	Remote Similarity	NPD6012	Approved
0.6379	Remote Similarity	NPD6013	Approved
0.6355	Remote Similarity	NPD6411	Approved
0.6354	Remote Similarity	NPD4732	Discontinued
0.6349	Remote Similarity	NPD7078	Approved
0.6348	Remote Similarity	NPD6412	Phase 2
0.6348	Remote Similarity	NPD5701	Approved
0.6348	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5983	Phase 2
0.6341	Remote Similarity	NPD6015	Approved
0.6341	Remote Similarity	NPD6016	Approved
0.6337	Remote Similarity	NPD6898	Phase 1
0.633	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6933	Approved
0.6325	Remote Similarity	NPD6883	Approved
0.6325	Remote Similarity	NPD7290	Approved
0.6325	Remote Similarity	NPD7102	Approved
0.6299	Remote Similarity	NPD7736	Approved
0.6293	Remote Similarity	NPD7320	Approved
0.6293	Remote Similarity	NPD6011	Approved
0.629	Remote Similarity	NPD5988	Approved
0.629	Remote Similarity	NPD6370	Approved
0.6283	Remote Similarity	NPD5211	Phase 2
0.6271	Remote Similarity	NPD6650	Approved
0.6271	Remote Similarity	NPD6847	Approved
0.6271	Remote Similarity	NPD6649	Approved
0.6271	Remote Similarity	NPD6869	Approved
0.6271	Remote Similarity	NPD8130	Phase 1
0.6271	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6617	Approved
0.626	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD1694	Approved
0.624	Remote Similarity	NPD7604	Phase 2
0.6239	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD7748	Approved
0.6238	Remote Similarity	NPD7525	Registered
0.6238	Remote Similarity	NPD4819	Approved
0.6238	Remote Similarity	NPD4821	Approved
0.6238	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4822	Approved
0.6238	Remote Similarity	NPD4820	Approved
0.622	Remote Similarity	NPD8074	Phase 3
0.622	Remote Similarity	NPD8293	Discontinued
0.6218	Remote Similarity	NPD6882	Approved
0.6216	Remote Similarity	NPD7902	Approved
0.6204	Remote Similarity	NPD7515	Phase 2
0.62	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4634	Approved
0.6174	Remote Similarity	NPD5141	Approved
0.6168	Remote Similarity	NPD6101	Approved
0.6168	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6399	Phase 3
0.6142	Remote Similarity	NPD6336	Discontinued
0.6139	Remote Similarity	NPD6683	Phase 2
0.6132	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6924	Approved
0.6122	Remote Similarity	NPD6926	Approved
0.6121	Remote Similarity	NPD6640	Phase 3
0.6121	Remote Similarity	NPD5357	Phase 1
0.6117	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8328	Phase 3
0.6106	Remote Similarity	NPD5286	Approved
0.6106	Remote Similarity	NPD4696	Approved
0.6106	Remote Similarity	NPD5285	Approved
0.6083	Remote Similarity	NPD6053	Discontinued
0.608	Remote Similarity	NPD6921	Approved
0.6078	Remote Similarity	NPD7509	Discontinued
0.6071	Remote Similarity	NPD6084	Phase 2
0.6071	Remote Similarity	NPD4755	Approved
0.6071	Remote Similarity	NPD6083	Phase 2
0.6071	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7154	Phase 3
0.6055	Remote Similarity	NPD5281	Approved
0.6055	Remote Similarity	NPD5284	Approved
0.6053	Remote Similarity	NPD4159	Approved
0.604	Remote Similarity	NPD4268	Approved
0.604	Remote Similarity	NPD4271	Approved
0.6038	Remote Similarity	NPD3618	Phase 1
0.6036	Remote Similarity	NPD5695	Phase 3
0.6033	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD5224	Approved
0.5982	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7839	Suspended
0.598	Remote Similarity	NPD7645	Phase 2
0.5979	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4194	Approved
0.5978	Remote Similarity	NPD4193	Approved
0.5978	Remote Similarity	NPD4192	Approved
0.5978	Remote Similarity	NPD4191	Approved
0.5965	Remote Similarity	NPD4700	Approved
0.5963	Remote Similarity	NPD5785	Approved
0.5963	Remote Similarity	NPD7136	Phase 2
0.5948	Remote Similarity	NPD5175	Approved
0.5948	Remote Similarity	NPD5174	Approved
0.5946	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7900	Approved
0.5943	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD6274	Approved
0.5922	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7100	Approved
0.592	Remote Similarity	NPD7101	Approved
0.5918	Remote Similarity	NPD7151	Approved
0.5918	Remote Similarity	NPD7150	Approved
0.5918	Remote Similarity	NPD7152	Approved
0.5913	Remote Similarity	NPD5223	Approved
0.5909	Remote Similarity	NPD6079	Approved
0.5909	Remote Similarity	NPD7260	Phase 2
0.5905	Remote Similarity	NPD5362	Discontinued
0.5905	Remote Similarity	NPD6110	Phase 1
0.5888	Remote Similarity	NPD5279	Phase 3
0.5887	Remote Similarity	NPD7505	Discontinued
0.5887	Remote Similarity	NPD8295	Clinical (unspecified phase)

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