NPASS Compound

Structure

NPC189311 OpenBabel07101719252D 27 29 0 0 1 0 0 0 0 0999 V2000 5.7280 2.3082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5940 -1.1918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7280 1.3082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1265 -1.6832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3229 -1.1401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7280 -0.6918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5799 -1.5106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0300 -0.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7280 0.3082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9960 2.3082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1299 0.8082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8620 -2.1918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8620 1.8082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5940 -2.1918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3570 -0.8812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8620 -1.1918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1299 1.8082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9960 0.3082 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9986 0.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8620 0.8082 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9960 -0.6918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4601 -2.6918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2639 2.3082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5433 0.8910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7280 -2.6918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 10 1 0 0 0 0 7 16 2 0 0 0 0 8 22 1 0 0 0 0 9 21 1 0 0 0 0 10 26 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 27 1 0 0 0 0 14 21 1 0 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 16 20 1 0 0 0 0 17 22 1 1 0 0 0 18 24 2 0 0 0 0 19 21 1 6 0 0 0 19 22 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 3 1 6 0 0 0 22 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	394.168
LogP:	3.477
LogD:	2.924
LogS:	-3.885
# Rotatable Bonds:	6
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.771
Synthetic Accessibility Score:	4.453
Fsp3:	0.636
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:	-5.108
MDCK Permeability:	2.8335449314909056e-05
Pgp-inhibitor:	0.726
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.134
30% Bioavailability (F30%):	0.087

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	89.32762908935547%
Volume Distribution (VD):	0.645
Pgp-substrate:	8.528254508972168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.241
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.349
CYP2C9-inhibitor:	0.104
CYP2C9-substrate:	0.145
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.194
CYP3A4-inhibitor:	0.286
CYP3A4-substrate:	0.404

ADMET: Excretion

Clearance (CL):	16.35
Half-life (T1/2):	0.88

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.466
Drug-inuced Liver Injury (DILI):	0.17
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.384
Maximum Recommended Daily Dose:	0.525
Skin Sensitization:	0.657
Carcinogencity:	0.802
Eye Corrosion:	0.019
Eye Irritation:	0.13
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: NPC189311

Natural Product ID:	NPC189311
*Common Name:**	Gomphostenin A
IUPAC Name:	[(1S,2R,4aS,8aS)-1,4a,5-trimethyl-7-oxo-1-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,8,8a-tetrahydro-2H-naphthalen-2-yl]methyl acetate
Synonyms:	Gomphostenin-A
Standard InCHIKey:	FCMMTMZFACYHCP-RGMHLJPOSA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-14-11-18(24)12-19-21(14,3)9-6-17(13-27-15(2)23)22(19,4)8-5-16-7-10-26-20(16)25/h7,11,17,19H,5-6,8-10,12-13H2,1-4H3/t17-,19+,21+,22+/m0/s1
SMILES:	CC(=O)OC[C@@H]1CC[C@]2([C@H]([C@]1(C)CCC1=CCOC1=O)CC(=O)C=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL597328
PubChem CID:	46216680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO2879	Gomphostemma niveum	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20022506]
NPO2879	Gomphostemma niveum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
Others	1

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3.4	ug.mL-1	PMID[527150]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3.2	ug.mL-1	PMID[527150]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	45.0	%	PMID[527151]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8800.0	nM	PMID[527151]

☑ 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 NPC189311 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	191
0.1-0.2	1174
0.2-0.3	4691
0.3-0.4	11985
0.4-0.5	10779
0.5-0.6	7092
0.6-0.7	4937
0.7-0.8	1655
0.8-0.85	146
0.85-0.9	38
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC5509
0.9398	High Similarity	NPC226863
0.9375	High Similarity	NPC200513
0.9259	High Similarity	NPC193198
0.9146	High Similarity	NPC30486
0.9146	High Similarity	NPC149869
0.9036	High Similarity	NPC65661
0.9024	High Similarity	NPC22611
0.9012	High Similarity	NPC282293
0.8987	High Similarity	NPC316500
0.8966	High Similarity	NPC475657
0.8953	High Similarity	NPC51486
0.8941	High Similarity	NPC472302
0.8929	High Similarity	NPC220478
0.8916	High Similarity	NPC475100
0.8875	High Similarity	NPC471220
0.8837	High Similarity	NPC174342
0.8837	High Similarity	NPC284561
0.881	High Similarity	NPC106416
0.881	High Similarity	NPC86316
0.8795	High Similarity	NPC118423
0.8765	High Similarity	NPC150646
0.8764	High Similarity	NPC295347
0.875	High Similarity	NPC115021
0.8736	High Similarity	NPC220454
0.8736	High Similarity	NPC212679
0.8736	High Similarity	NPC8062
0.8736	High Similarity	NPC469595
0.8721	High Similarity	NPC215831
0.8706	High Similarity	NPC168248
0.869	High Similarity	NPC71626
0.8675	High Similarity	NPC186276
0.8675	High Similarity	NPC268122
0.8659	High Similarity	NPC195424
0.8652	High Similarity	NPC470697
0.8652	High Similarity	NPC477129
0.8652	High Similarity	NPC477130
0.8652	High Similarity	NPC84893
0.8636	High Similarity	NPC65513
0.8625	High Similarity	NPC40353
0.8625	High Similarity	NPC27205
0.8621	High Similarity	NPC168131
0.8621	High Similarity	NPC73995
0.8605	High Similarity	NPC312561
0.8605	High Similarity	NPC477228
0.8588	High Similarity	NPC177932
0.8571	High Similarity	NPC84335
0.8571	High Similarity	NPC208094
0.8571	High Similarity	NPC38530
0.8556	High Similarity	NPC209355
0.8539	High Similarity	NPC139692
0.8523	High Similarity	NPC159748
0.8523	High Similarity	NPC152467
0.8523	High Similarity	NPC101651
0.8523	High Similarity	NPC232426
0.8523	High Similarity	NPC471818
0.8523	High Similarity	NPC281942
0.8519	High Similarity	NPC472300
0.8506	High Similarity	NPC477128
0.85	High Similarity	NPC65650
0.8471	Intermediate Similarity	NPC474359
0.8452	Intermediate Similarity	NPC94200
0.8452	Intermediate Similarity	NPC178676
0.8452	Intermediate Similarity	NPC471218
0.8444	Intermediate Similarity	NPC38830
0.8444	Intermediate Similarity	NPC476596
0.8444	Intermediate Similarity	NPC476415
0.8427	Intermediate Similarity	NPC472814
0.8427	Intermediate Similarity	NPC473944
0.8427	Intermediate Similarity	NPC477783
0.8427	Intermediate Similarity	NPC141831
0.8427	Intermediate Similarity	NPC177037
0.8415	Intermediate Similarity	NPC128276
0.8409	Intermediate Similarity	NPC177141
0.8409	Intermediate Similarity	NPC251528
0.8395	Intermediate Similarity	NPC473223
0.8387	Intermediate Similarity	NPC474012
0.8387	Intermediate Similarity	NPC54705
0.8387	Intermediate Similarity	NPC476299
0.8375	Intermediate Similarity	NPC20025
0.8372	Intermediate Similarity	NPC323765
0.8372	Intermediate Similarity	NPC472442
0.8372	Intermediate Similarity	NPC110405
0.837	Intermediate Similarity	NPC476253
0.8353	Intermediate Similarity	NPC472440
0.8353	Intermediate Similarity	NPC477124
0.8352	Intermediate Similarity	NPC183012
0.8352	Intermediate Similarity	NPC33473
0.8333	Intermediate Similarity	NPC476598
0.8333	Intermediate Similarity	NPC229584
0.8333	Intermediate Similarity	NPC472303
0.8333	Intermediate Similarity	NPC40228
0.8333	Intermediate Similarity	NPC475665
0.8333	Intermediate Similarity	NPC14203
0.8333	Intermediate Similarity	NPC476597
0.8315	Intermediate Similarity	NPC476369
0.8315	Intermediate Similarity	NPC476437
0.8315	Intermediate Similarity	NPC477782
0.8315	Intermediate Similarity	NPC469372
0.8313	Intermediate Similarity	NPC471299
0.8298	Intermediate Similarity	NPC310981
0.8295	Intermediate Similarity	NPC196407
0.8293	Intermediate Similarity	NPC57744
0.8276	Intermediate Similarity	NPC195640
0.8261	Intermediate Similarity	NPC134072
0.8261	Intermediate Similarity	NPC319692
0.8261	Intermediate Similarity	NPC325960
0.8261	Intermediate Similarity	NPC112654
0.8261	Intermediate Similarity	NPC242848
0.8261	Intermediate Similarity	NPC29952
0.8261	Intermediate Similarity	NPC234993
0.8242	Intermediate Similarity	NPC53685
0.8242	Intermediate Similarity	NPC148463
0.8229	Intermediate Similarity	NPC189616
0.8222	Intermediate Similarity	NPC303697
0.8222	Intermediate Similarity	NPC289479
0.8214	Intermediate Similarity	NPC474956
0.8202	Intermediate Similarity	NPC285982
0.8202	Intermediate Similarity	NPC173042
0.8193	Intermediate Similarity	NPC74410
0.8191	Intermediate Similarity	NPC117685
0.8191	Intermediate Similarity	NPC471413
0.8182	Intermediate Similarity	NPC181327
0.8172	Intermediate Similarity	NPC53844
0.8172	Intermediate Similarity	NPC475709
0.8172	Intermediate Similarity	NPC476768
0.8172	Intermediate Similarity	NPC110937
0.8172	Intermediate Similarity	NPC2049
0.8172	Intermediate Similarity	NPC204054
0.8172	Intermediate Similarity	NPC474343
0.8172	Intermediate Similarity	NPC257726
0.8172	Intermediate Similarity	NPC253826
0.8171	Intermediate Similarity	NPC180886
0.8161	Intermediate Similarity	NPC2709
0.8161	Intermediate Similarity	NPC474013
0.8161	Intermediate Similarity	NPC30984
0.8152	Intermediate Similarity	NPC171395
0.8152	Intermediate Similarity	NPC293052
0.8152	Intermediate Similarity	NPC473369
0.8152	Intermediate Similarity	NPC127197
0.8144	Intermediate Similarity	NPC127790
0.814	Intermediate Similarity	NPC222358
0.814	Intermediate Similarity	NPC470046
0.814	Intermediate Similarity	NPC474976
0.814	Intermediate Similarity	NPC474790
0.814	Intermediate Similarity	NPC470047
0.814	Intermediate Similarity	NPC49019
0.814	Intermediate Similarity	NPC97913
0.814	Intermediate Similarity	NPC474193
0.814	Intermediate Similarity	NPC12283
0.8132	Intermediate Similarity	NPC472871
0.8132	Intermediate Similarity	NPC469939
0.8132	Intermediate Similarity	NPC166346
0.8132	Intermediate Similarity	NPC229976
0.8132	Intermediate Similarity	NPC476416
0.8132	Intermediate Similarity	NPC169343
0.8125	Intermediate Similarity	NPC257618
0.8118	Intermediate Similarity	NPC149237
0.8118	Intermediate Similarity	NPC90055
0.8118	Intermediate Similarity	NPC42470
0.8118	Intermediate Similarity	NPC327002
0.8118	Intermediate Similarity	NPC471325
0.8118	Intermediate Similarity	NPC278459
0.8111	Intermediate Similarity	NPC161638
0.8111	Intermediate Similarity	NPC475965
0.8111	Intermediate Similarity	NPC474842
0.8111	Intermediate Similarity	NPC198818
0.8111	Intermediate Similarity	NPC273199
0.8105	Intermediate Similarity	NPC471412
0.8105	Intermediate Similarity	NPC472643
0.8105	Intermediate Similarity	NPC168319
0.8105	Intermediate Similarity	NPC194028
0.8095	Intermediate Similarity	NPC327674
0.8095	Intermediate Similarity	NPC178277
0.809	Intermediate Similarity	NPC24816
0.809	Intermediate Similarity	NPC472870
0.8085	Intermediate Similarity	NPC108368
0.8085	Intermediate Similarity	NPC316598
0.8085	Intermediate Similarity	NPC23364
0.8085	Intermediate Similarity	NPC98868
0.8085	Intermediate Similarity	NPC57079
0.8085	Intermediate Similarity	NPC252295
0.8085	Intermediate Similarity	NPC176845
0.8072	Intermediate Similarity	NPC54996
0.8072	Intermediate Similarity	NPC41780
0.8072	Intermediate Similarity	NPC189206
0.8072	Intermediate Similarity	NPC187568
0.8072	Intermediate Similarity	NPC97377
0.8068	Intermediate Similarity	NPC471219
0.8068	Intermediate Similarity	NPC474062
0.8068	Intermediate Similarity	NPC470051
0.8068	Intermediate Similarity	NPC470050
0.8065	Intermediate Similarity	NPC202833
0.8049	Intermediate Similarity	NPC244166
0.8046	Intermediate Similarity	NPC472865
0.8046	Intermediate Similarity	NPC318515
0.8046	Intermediate Similarity	NPC100391
0.8046	Intermediate Similarity	NPC164577
0.8043	Intermediate Similarity	NPC474554
0.8023	Intermediate Similarity	NPC321289

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 NPC189311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1470
0.2-0.3	3817
0.3-0.4	2384
0.4-0.5	817
0.5-0.6	284
0.6-0.7	158
0.7-0.8	46
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9375	High Similarity	NPD4752	Clinical (unspecified phase)
0.8588	High Similarity	NPD1694	Approved
0.8295	Intermediate Similarity	NPD6672	Approved
0.8295	Intermediate Similarity	NPD5737	Approved
0.8276	Intermediate Similarity	NPD7521	Approved
0.8276	Intermediate Similarity	NPD6684	Approved
0.8276	Intermediate Similarity	NPD6409	Approved
0.8276	Intermediate Similarity	NPD5330	Approved
0.8276	Intermediate Similarity	NPD7146	Approved
0.8276	Intermediate Similarity	NPD7334	Approved
0.8222	Intermediate Similarity	NPD5693	Phase 1
0.809	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD6903	Approved
0.7802	Intermediate Similarity	NPD6673	Approved
0.7802	Intermediate Similarity	NPD6080	Approved
0.7802	Intermediate Similarity	NPD6904	Approved
0.7778	Intermediate Similarity	NPD3573	Approved
0.7766	Intermediate Similarity	NPD5695	Phase 3
0.7717	Intermediate Similarity	NPD5692	Phase 3
0.7692	Intermediate Similarity	NPD5208	Approved
0.766	Intermediate Similarity	NPD7748	Approved
0.766	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7900	Approved
0.7634	Intermediate Similarity	NPD5694	Approved
0.7634	Intermediate Similarity	NPD6050	Approved
0.7619	Intermediate Similarity	NPD8039	Approved
0.7604	Intermediate Similarity	NPD6083	Phase 2
0.7604	Intermediate Similarity	NPD6084	Phase 2
0.7579	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD6399	Phase 3
0.7527	Intermediate Similarity	NPD5207	Approved
0.7526	Intermediate Similarity	NPD5696	Approved
0.7526	Intermediate Similarity	NPD7638	Approved
0.7473	Intermediate Similarity	NPD6098	Approved
0.7451	Intermediate Similarity	NPD6686	Approved
0.7449	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD7639	Approved
0.7447	Intermediate Similarity	NPD7515	Phase 2
0.7444	Intermediate Similarity	NPD3666	Approved
0.7444	Intermediate Similarity	NPD3665	Phase 1
0.7444	Intermediate Similarity	NPD3133	Approved
0.7423	Intermediate Similarity	NPD7902	Approved
0.7419	Intermediate Similarity	NPD6051	Approved
0.7416	Intermediate Similarity	NPD5209	Approved
0.7386	Intermediate Similarity	NPD4695	Discontinued
0.7349	Intermediate Similarity	NPD4691	Approved
0.7347	Intermediate Similarity	NPD4225	Approved
0.7292	Intermediate Similarity	NPD6001	Approved
0.7283	Intermediate Similarity	NPD3618	Phase 1
0.7283	Intermediate Similarity	NPD4519	Discontinued
0.7283	Intermediate Similarity	NPD4623	Approved
0.7263	Intermediate Similarity	NPD5281	Approved
0.7263	Intermediate Similarity	NPD5284	Approved
0.7253	Intermediate Similarity	NPD3668	Phase 3
0.7234	Intermediate Similarity	NPD4753	Phase 2
0.7229	Intermediate Similarity	NPD4137	Phase 3
0.7222	Intermediate Similarity	NPD4223	Phase 3
0.7222	Intermediate Similarity	NPD7115	Discovery
0.7222	Intermediate Similarity	NPD4221	Approved
0.7222	Intermediate Similarity	NPD3667	Approved
0.7216	Intermediate Similarity	NPD5654	Approved
0.7184	Intermediate Similarity	NPD5697	Approved
0.7184	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5785	Approved
0.7143	Intermediate Similarity	NPD7732	Phase 3
0.7143	Intermediate Similarity	NPD4747	Approved
0.7115	Intermediate Similarity	NPD6899	Approved
0.7115	Intermediate Similarity	NPD6881	Approved
0.7115	Intermediate Similarity	NPD6011	Approved
0.7097	Intermediate Similarity	NPD5279	Phase 3
0.7097	Intermediate Similarity	NPD5690	Phase 2
0.7097	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4058	Approved
0.7087	Intermediate Similarity	NPD6402	Approved
0.7087	Intermediate Similarity	NPD6008	Approved
0.7087	Intermediate Similarity	NPD5739	Approved
0.7087	Intermediate Similarity	NPD7128	Approved
0.7087	Intermediate Similarity	NPD6675	Approved
0.7083	Intermediate Similarity	NPD6079	Approved
0.7071	Intermediate Similarity	NPD5959	Approved
0.7065	Intermediate Similarity	NPD4197	Approved
0.7065	Intermediate Similarity	NPD4786	Approved
0.7053	Intermediate Similarity	NPD5328	Approved
0.7053	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6014	Approved
0.7048	Intermediate Similarity	NPD6012	Approved
0.7048	Intermediate Similarity	NPD6013	Approved
0.7041	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4629	Approved
0.7041	Intermediate Similarity	NPD5210	Approved
0.7019	Intermediate Similarity	NPD5701	Approved
0.6989	Remote Similarity	NPD5329	Approved
0.6981	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7290	Approved
0.6981	Remote Similarity	NPD6883	Approved
0.6981	Remote Similarity	NPD7102	Approved
0.697	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5221	Approved
0.697	Remote Similarity	NPD5222	Approved
0.6966	Remote Similarity	NPD3617	Approved
0.6952	Remote Similarity	NPD7320	Approved
0.6916	Remote Similarity	NPD6650	Approved
0.6916	Remote Similarity	NPD8130	Phase 1
0.6916	Remote Similarity	NPD6617	Approved
0.6916	Remote Similarity	NPD6869	Approved
0.6916	Remote Similarity	NPD6649	Approved
0.6916	Remote Similarity	NPD6847	Approved
0.6915	Remote Similarity	NPD5280	Approved
0.6915	Remote Similarity	NPD4690	Approved
0.6915	Remote Similarity	NPD4689	Approved
0.6915	Remote Similarity	NPD4693	Phase 3
0.6915	Remote Similarity	NPD4138	Approved
0.6915	Remote Similarity	NPD5205	Approved
0.6915	Remote Similarity	NPD4694	Approved
0.6915	Remote Similarity	NPD4688	Approved
0.69	Remote Similarity	NPD5173	Approved
0.6897	Remote Similarity	NPD5733	Approved
0.6897	Remote Similarity	NPD4687	Approved
0.6893	Remote Similarity	NPD6052	Approved
0.6887	Remote Similarity	NPD6372	Approved
0.6887	Remote Similarity	NPD6373	Approved
0.6882	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5276	Approved
0.6857	Remote Similarity	NPD6614	Approved
0.6852	Remote Similarity	NPD6882	Approved
0.6852	Remote Similarity	NPD8297	Approved
0.6837	Remote Similarity	NPD4202	Approved
0.68	Remote Similarity	NPD7614	Phase 1
0.68	Remote Similarity	NPD4697	Phase 3
0.6796	Remote Similarity	NPD5211	Phase 2
0.6796	Remote Similarity	NPD7632	Discontinued
0.6778	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5285	Approved
0.6765	Remote Similarity	NPD5286	Approved
0.6765	Remote Similarity	NPD4696	Approved
0.6765	Remote Similarity	NPD6404	Discontinued
0.6759	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6411	Approved
0.6733	Remote Similarity	NPD4755	Approved
0.6706	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4195	Approved
0.6699	Remote Similarity	NPD5223	Approved
0.6698	Remote Similarity	NPD6412	Phase 2
0.6697	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD4632	Approved
0.6635	Remote Similarity	NPD4633	Approved
0.6635	Remote Similarity	NPD5224	Approved
0.6635	Remote Similarity	NPD5226	Approved
0.6635	Remote Similarity	NPD5225	Approved
0.6633	Remote Similarity	NPD6698	Approved
0.6633	Remote Similarity	NPD46	Approved
0.6632	Remote Similarity	NPD5363	Approved
0.6627	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6317	Approved
0.6602	Remote Similarity	NPD4700	Approved
0.6596	Remote Similarity	NPD4788	Approved
0.6571	Remote Similarity	NPD5174	Approved
0.6571	Remote Similarity	NPD5175	Approved
0.6566	Remote Similarity	NPD8034	Phase 2
0.6566	Remote Similarity	NPD8035	Phase 2
0.6549	Remote Similarity	NPD6314	Approved
0.6549	Remote Similarity	NPD6335	Approved
0.6549	Remote Similarity	NPD6313	Approved
0.6531	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1695	Approved
0.6531	Remote Similarity	NPD6101	Approved
0.6514	Remote Similarity	NPD6371	Approved
0.6491	Remote Similarity	NPD7101	Approved
0.6491	Remote Similarity	NPD7100	Approved
0.6486	Remote Similarity	NPD6858	Approved
0.6486	Remote Similarity	NPD7094	Approved
0.6484	Remote Similarity	NPD4756	Discovery
0.6477	Remote Similarity	NPD5777	Approved
0.6465	Remote Similarity	NPD4096	Approved
0.646	Remote Similarity	NPD6009	Approved
0.6458	Remote Similarity	NPD1696	Phase 3
0.6458	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7507	Approved
0.6435	Remote Similarity	NPD6319	Approved
0.6421	Remote Similarity	NPD5362	Discontinued
0.6421	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7154	Phase 3
0.642	Remote Similarity	NPD287	Approved
0.6415	Remote Similarity	NPD4754	Approved
0.64	Remote Similarity	NPD7637	Suspended
0.6383	Remote Similarity	NPD4692	Approved
0.6383	Remote Similarity	NPD4139	Approved
0.6379	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5983	Phase 2
0.6337	Remote Similarity	NPD5133	Approved
0.633	Remote Similarity	NPD5128	Approved
0.633	Remote Similarity	NPD4730	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