NPASS Compound

Structure

CID326264 OpenBabel06191716182D 39 42 0 0 1 0 0 0 0 0999 V2000 5.6621 -6.6121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7058 -7.0280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4112 -5.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0585 -6.4927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9929 -5.8690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3457 -5.3338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6984 -4.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0148 -6.0769 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.7202 -5.0064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3675 -5.5417 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.2812 -2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -4.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0132 -4.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -4.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -3.3090 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 1 7 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 7 17 1 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 24 1 0 0 0 0 10 17 1 0 0 0 0 10 19 1 0 0 0 0 11 18 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 13 26 2 0 0 0 0 14 21 2 0 0 0 0 14 27 1 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 23 2 0 0 0 0 16 38 1 0 0 0 0 20 5 1 1 0 0 0 20 28 1 0 0 0 0 21 23 1 0 0 0 0 22 33 1 1 0 0 0 23 30 1 0 0 0 0 24 34 2 0 0 0 0 25 28 1 0 0 0 0 25 35 2 0 0 0 0 26 38 1 0 0 0 0 27 32 1 0 0 0 0 27 36 2 0 0 0 0 28 26 1 6 0 0 0 29 24 1 1 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 30 32 1 1 0 0 0 31 37 2 0 0 0 0 31 39 1 0 0 0 0 32 6 1 6 0 0 0 32 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.28
Volume:	565.606
LogP:	4.144
LogD:	1.652
LogS:	-4.842
# Rotatable Bonds:	8
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.261
Synthetic Accessibility Score:	5.668
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.035
MDCK Permeability:	1.7715989088173956e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.878
Human Intestinal Absorption (HIA):	0.487
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.634
Plasma Protein Binding (PPB):	76.79134368896484%
Volume Distribution (VD):	1.622
Pgp-substrate:	18.54607391357422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.484
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.741
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.7

ADMET: Excretion

Clearance (CL):	5.587
Half-life (T1/2):	0.607

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.86
Drug-inuced Liver Injury (DILI):	0.173
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.929
Carcinogencity:	0.838
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.347

Download Data

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

Natural Product: NPC326264

Natural Product ID:	NPC326264
*Common Name:**	Longirostreronea
IUPAC Name:	(6aR,9S,9aR)-3-[(1S,2S,4R)-4-hydroxy-2-methyl-6-oxocyclohexyl]-6a-methyl-9-[(2E,4E)-4,6,8-trimethyldeca-2,4-dienoyl]-9,9a-dihydrofuro[2,3-h]isochromene-6,8-dione
Synonyms:	longirostreroneA
Standard InCHIKey:	IAPUSMZQQSXGDI-QXHNIIHBSA-N
Standard InCHI:	InChI=1S/C32H40O7/c1-7-17(2)10-19(4)11-18(3)8-9-24(34)29-30-23-16-38-26(28-20(5)12-22(33)15-25(28)35)13-21(23)14-27(36)32(30,6)39-31(29)37/h8-9,11,13-14,16-17,19-20,22,28-30,33H,7,10,12,15H2,1-6H3/b9-8+,18-11+/t17?,19?,20-,22+,28+,29+,30-,32-/m0/s1
SMILES:	CCC(CC(/C=C(/C=C/C(=O)[C@H]1C(=O)O[C@@]2([C@H]1C1=COC(=CC1=CC2=O)[C@@H]1[C@@H](C)C[C@H](CC1=O)O)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1939684
PubChem CID:	56833382
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO31373	Chaetomium longirostre	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22004007]

☑ 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	4

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1040.0	nM	PMID[498278]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	240.0	nM	PMID[498278]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	3080.0	nM	PMID[498278]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	630.0	nM	PMID[498278]

☑ 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 NPC326264 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	202
0.1-0.2	1119
0.2-0.3	3993
0.3-0.4	8271
0.4-0.5	13860
0.5-0.6	9670
0.6-0.7	4974
0.7-0.8	594
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9135	High Similarity	NPC320294
0.9083	High Similarity	NPC321496
0.8545	High Similarity	NPC23497
0.8435	Intermediate Similarity	NPC21326
0.8381	Intermediate Similarity	NPC318082
0.8286	Intermediate Similarity	NPC31021
0.8205	Intermediate Similarity	NPC472933
0.819	Intermediate Similarity	NPC472927
0.8091	Intermediate Similarity	NPC271059
0.8091	Intermediate Similarity	NPC25666
0.8087	Intermediate Similarity	NPC474271
0.807	Intermediate Similarity	NPC34315
0.8053	Intermediate Similarity	NPC250018
0.8034	Intermediate Similarity	NPC472934
0.8017	Intermediate Similarity	NPC247069
0.7983	Intermediate Similarity	NPC476815
0.7982	Intermediate Similarity	NPC472972
0.7931	Intermediate Similarity	NPC472929
0.7931	Intermediate Similarity	NPC472926
0.7928	Intermediate Similarity	NPC275583
0.7899	Intermediate Similarity	NPC268958
0.7899	Intermediate Similarity	NPC470777
0.7833	Intermediate Similarity	NPC478051
0.7833	Intermediate Similarity	NPC31641
0.7826	Intermediate Similarity	NPC210005
0.7815	Intermediate Similarity	NPC17772
0.7797	Intermediate Similarity	NPC270478
0.7797	Intermediate Similarity	NPC270958
0.7788	Intermediate Similarity	NPC469607
0.7778	Intermediate Similarity	NPC198539
0.776	Intermediate Similarity	NPC221414
0.7759	Intermediate Similarity	NPC231589
0.7759	Intermediate Similarity	NPC214797
0.7759	Intermediate Similarity	NPC472928
0.7759	Intermediate Similarity	NPC118860
0.775	Intermediate Similarity	NPC245320
0.7739	Intermediate Similarity	NPC304495
0.7731	Intermediate Similarity	NPC239273
0.7727	Intermediate Similarity	NPC472687
0.7727	Intermediate Similarity	NPC471330
0.7727	Intermediate Similarity	NPC203388
0.7727	Intermediate Similarity	NPC471331
0.7727	Intermediate Similarity	NPC99657
0.7724	Intermediate Similarity	NPC24651
0.7719	Intermediate Similarity	NPC144854
0.7719	Intermediate Similarity	NPC3316
0.7712	Intermediate Similarity	NPC473798
0.7706	Intermediate Similarity	NPC269492
0.7699	Intermediate Similarity	NPC96268
0.7699	Intermediate Similarity	NPC213366
0.7692	Intermediate Similarity	NPC71348
0.7692	Intermediate Similarity	NPC193948
0.7692	Intermediate Similarity	NPC170487
0.7686	Intermediate Similarity	NPC473145
0.7679	Intermediate Similarity	NPC31058
0.7679	Intermediate Similarity	NPC469606
0.7679	Intermediate Similarity	NPC273005
0.7672	Intermediate Similarity	NPC129689
0.7672	Intermediate Similarity	NPC286880
0.7672	Intermediate Similarity	NPC478209
0.7667	Intermediate Similarity	NPC297179
0.7667	Intermediate Similarity	NPC118638
0.7658	Intermediate Similarity	NPC472727
0.7658	Intermediate Similarity	NPC472728
0.7658	Intermediate Similarity	NPC46761
0.7652	Intermediate Similarity	NPC476802
0.7652	Intermediate Similarity	NPC154608
0.7652	Intermediate Similarity	NPC89171
0.7652	Intermediate Similarity	NPC192813
0.7652	Intermediate Similarity	NPC277017
0.7647	Intermediate Similarity	NPC251236
0.7647	Intermediate Similarity	NPC16081
0.7647	Intermediate Similarity	NPC173686
0.7647	Intermediate Similarity	NPC328374
0.7647	Intermediate Similarity	NPC207217
0.7647	Intermediate Similarity	NPC40632
0.7647	Intermediate Similarity	NPC96312
0.7642	Intermediate Similarity	NPC265557
0.7642	Intermediate Similarity	NPC18945
0.7642	Intermediate Similarity	NPC105926
0.7642	Intermediate Similarity	NPC91693
0.7636	Intermediate Similarity	NPC273269
0.7636	Intermediate Similarity	NPC27105
0.7632	Intermediate Similarity	NPC181357
0.7632	Intermediate Similarity	NPC471332
0.7632	Intermediate Similarity	NPC32006
0.7632	Intermediate Similarity	NPC478208
0.7632	Intermediate Similarity	NPC471333
0.7632	Intermediate Similarity	NPC85529
0.7632	Intermediate Similarity	NPC292588
0.7627	Intermediate Similarity	NPC469454
0.7627	Intermediate Similarity	NPC25909
0.7627	Intermediate Similarity	NPC469463
0.7627	Intermediate Similarity	NPC469496
0.7627	Intermediate Similarity	NPC159333
0.7627	Intermediate Similarity	NPC202889
0.7611	Intermediate Similarity	NPC179208
0.7611	Intermediate Similarity	NPC159442
0.7607	Intermediate Similarity	NPC324683
0.7607	Intermediate Similarity	NPC43775
0.7607	Intermediate Similarity	NPC115303
0.76	Intermediate Similarity	NPC476008
0.7589	Intermediate Similarity	NPC469851
0.7586	Intermediate Similarity	NPC286174
0.7586	Intermediate Similarity	NPC20192
0.7586	Intermediate Similarity	NPC153239
0.7586	Intermediate Similarity	NPC258543
0.7586	Intermediate Similarity	NPC27814
0.7586	Intermediate Similarity	NPC77947
0.7586	Intermediate Similarity	NPC241927
0.7583	Intermediate Similarity	NPC470854
0.7583	Intermediate Similarity	NPC474654
0.7583	Intermediate Similarity	NPC122033
0.7583	Intermediate Similarity	NPC287343
0.7583	Intermediate Similarity	NPC97908
0.7581	Intermediate Similarity	NPC476729
0.7568	Intermediate Similarity	NPC472729
0.7568	Intermediate Similarity	NPC472730
0.7568	Intermediate Similarity	NPC177680
0.7568	Intermediate Similarity	NPC153776
0.7565	Intermediate Similarity	NPC202524
0.7565	Intermediate Similarity	NPC475294
0.7565	Intermediate Similarity	NPC199107
0.7565	Intermediate Similarity	NPC472925
0.7565	Intermediate Similarity	NPC232969
0.7563	Intermediate Similarity	NPC143268
0.7563	Intermediate Similarity	NPC45218
0.7563	Intermediate Similarity	NPC323821
0.7563	Intermediate Similarity	NPC268238
0.7561	Intermediate Similarity	NPC312833
0.7544	Intermediate Similarity	NPC135854
0.7544	Intermediate Similarity	NPC216245
0.7544	Intermediate Similarity	NPC470251
0.7544	Intermediate Similarity	NPC2436
0.7542	Intermediate Similarity	NPC90769
0.7542	Intermediate Similarity	NPC66108
0.7542	Intermediate Similarity	NPC147180
0.7542	Intermediate Similarity	NPC264634
0.7541	Intermediate Similarity	NPC476962
0.7524	Intermediate Similarity	NPC203795
0.7522	Intermediate Similarity	NPC163249
0.7522	Intermediate Similarity	NPC53222
0.7521	Intermediate Similarity	NPC272898
0.7521	Intermediate Similarity	NPC5284
0.7521	Intermediate Similarity	NPC284707
0.7521	Intermediate Similarity	NPC106644
0.7521	Intermediate Similarity	NPC197428
0.7521	Intermediate Similarity	NPC473036
0.752	Intermediate Similarity	NPC477745
0.75	Intermediate Similarity	NPC102316
0.75	Intermediate Similarity	NPC322903
0.75	Intermediate Similarity	NPC100390
0.75	Intermediate Similarity	NPC476193
0.75	Intermediate Similarity	NPC67251
0.75	Intermediate Similarity	NPC120724
0.75	Intermediate Similarity	NPC54705
0.75	Intermediate Similarity	NPC275539
0.75	Intermediate Similarity	NPC478216
0.75	Intermediate Similarity	NPC148458
0.75	Intermediate Similarity	NPC235539
0.75	Intermediate Similarity	NPC254614
0.75	Intermediate Similarity	NPC152199
0.75	Intermediate Similarity	NPC189075
0.75	Intermediate Similarity	NPC104861
0.75	Intermediate Similarity	NPC476963
0.75	Intermediate Similarity	NPC134869
0.7481	Intermediate Similarity	NPC596
0.748	Intermediate Similarity	NPC470921
0.748	Intermediate Similarity	NPC54614
0.748	Intermediate Similarity	NPC309096
0.7479	Intermediate Similarity	NPC49451
0.7479	Intermediate Similarity	NPC478212
0.7479	Intermediate Similarity	NPC52634
0.7478	Intermediate Similarity	NPC96377
0.7478	Intermediate Similarity	NPC196528
0.7478	Intermediate Similarity	NPC102352
0.7478	Intermediate Similarity	NPC469852
0.7477	Intermediate Similarity	NPC472732
0.7477	Intermediate Similarity	NPC43747
0.7477	Intermediate Similarity	NPC256902
0.7477	Intermediate Similarity	NPC472731
0.7477	Intermediate Similarity	NPC118193
0.7459	Intermediate Similarity	NPC469488
0.7459	Intermediate Similarity	NPC476960
0.7458	Intermediate Similarity	NPC179798
0.7458	Intermediate Similarity	NPC171888
0.7458	Intermediate Similarity	NPC146945
0.7458	Intermediate Similarity	NPC207689
0.7458	Intermediate Similarity	NPC304180
0.7458	Intermediate Similarity	NPC474315
0.7458	Intermediate Similarity	NPC188738
0.7456	Intermediate Similarity	NPC282233
0.7456	Intermediate Similarity	NPC95585
0.7456	Intermediate Similarity	NPC95899
0.7456	Intermediate Similarity	NPC33973
0.7456	Intermediate Similarity	NPC70967
0.744	Intermediate Similarity	NPC470922
0.744	Intermediate Similarity	NPC8369
0.7438	Intermediate Similarity	NPC53396
0.7438	Intermediate Similarity	NPC243298

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 NPC326264 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1348
0.2-0.3	3664
0.3-0.4	2574
0.4-0.5	892
0.5-0.6	299
0.6-0.7	160
0.7-0.8	39
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
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.7458	Intermediate Similarity	NPD6649	Approved
0.7458	Intermediate Similarity	NPD8130	Phase 1
0.7458	Intermediate Similarity	NPD6650	Approved
0.744	Intermediate Similarity	NPD7492	Approved
0.7414	Intermediate Similarity	NPD5697	Approved
0.7402	Intermediate Similarity	NPD7736	Approved
0.7398	Intermediate Similarity	NPD6054	Approved
0.7398	Intermediate Similarity	NPD6319	Approved
0.7395	Intermediate Similarity	NPD8297	Approved
0.7381	Intermediate Similarity	NPD6616	Approved
0.7373	Intermediate Similarity	NPD7102	Approved
0.7373	Intermediate Similarity	NPD7290	Approved
0.7373	Intermediate Similarity	NPD6883	Approved
0.735	Intermediate Similarity	NPD6011	Approved
0.7328	Intermediate Similarity	NPD6402	Approved
0.7328	Intermediate Similarity	NPD5739	Approved
0.7328	Intermediate Similarity	NPD6675	Approved
0.7328	Intermediate Similarity	NPD7128	Approved
0.7323	Intermediate Similarity	NPD7078	Approved
0.7315	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6101	Approved
0.7311	Intermediate Similarity	NPD6847	Approved
0.7311	Intermediate Similarity	NPD6617	Approved
0.7311	Intermediate Similarity	NPD6869	Approved
0.7288	Intermediate Similarity	NPD6013	Approved
0.7288	Intermediate Similarity	NPD6014	Approved
0.7288	Intermediate Similarity	NPD6373	Approved
0.7288	Intermediate Similarity	NPD6012	Approved
0.7288	Intermediate Similarity	NPD6372	Approved
0.728	Intermediate Similarity	NPD6370	Approved
0.7273	Intermediate Similarity	NPD5779	Approved
0.7273	Intermediate Similarity	NPD5778	Approved
0.725	Intermediate Similarity	NPD6882	Approved
0.7203	Intermediate Similarity	NPD7320	Approved
0.72	Intermediate Similarity	NPD6015	Approved
0.72	Intermediate Similarity	NPD6016	Approved
0.719	Intermediate Similarity	NPD4632	Approved
0.7188	Intermediate Similarity	NPD8293	Discontinued
0.7182	Intermediate Similarity	NPD6411	Approved
0.7154	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD5988	Approved
0.712	Intermediate Similarity	NPD6059	Approved
0.7119	Intermediate Similarity	NPD5701	Approved
0.7105	Intermediate Similarity	NPD5696	Approved
0.7087	Intermediate Similarity	NPD7604	Phase 2
0.7087	Intermediate Similarity	NPD8328	Phase 3
0.7063	Intermediate Similarity	NPD5983	Phase 2
0.7054	Intermediate Similarity	NPD5282	Discontinued
0.7034	Intermediate Similarity	NPD6008	Approved
0.7025	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6083	Phase 2
0.7018	Intermediate Similarity	NPD6084	Phase 2
0.7016	Intermediate Similarity	NPD7115	Discovery
0.6977	Remote Similarity	NPD6336	Discontinued
0.6967	Remote Similarity	NPD6053	Discontinued
0.696	Remote Similarity	NPD6335	Approved
0.6942	Remote Similarity	NPD4634	Approved
0.6935	Remote Similarity	NPD6868	Approved
0.693	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5222	Approved
0.693	Remote Similarity	NPD5221	Approved
0.6929	Remote Similarity	NPD8513	Phase 3
0.6905	Remote Similarity	NPD7100	Approved
0.6905	Remote Similarity	NPD7101	Approved
0.6903	Remote Similarity	NPD7748	Approved
0.6897	Remote Similarity	NPD4696	Approved
0.6897	Remote Similarity	NPD5286	Approved
0.6897	Remote Similarity	NPD5285	Approved
0.688	Remote Similarity	NPD6317	Approved
0.6875	Remote Similarity	NPD6079	Approved
0.687	Remote Similarity	NPD7902	Approved
0.687	Remote Similarity	NPD5173	Approved
0.6842	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD7260	Phase 2
0.6842	Remote Similarity	NPD5210	Approved
0.6842	Remote Similarity	NPD5695	Phase 3
0.6838	Remote Similarity	NPD5223	Approved
0.6825	Remote Similarity	NPD6314	Approved
0.6825	Remote Similarity	NPD6313	Approved
0.6814	Remote Similarity	NPD6399	Phase 3
0.68	Remote Similarity	NPD6274	Approved
0.6797	Remote Similarity	NPD8517	Approved
0.6797	Remote Similarity	NPD8515	Approved
0.6797	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8516	Approved
0.6783	Remote Similarity	NPD4697	Phase 3
0.678	Remote Similarity	NPD5226	Approved
0.678	Remote Similarity	NPD5211	Phase 2
0.678	Remote Similarity	NPD4633	Approved
0.678	Remote Similarity	NPD5225	Approved
0.678	Remote Similarity	NPD5224	Approved
0.6777	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6672	Approved
0.6757	Remote Similarity	NPD5737	Approved
0.6746	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6033	Approved
0.6726	Remote Similarity	NPD6050	Approved
0.6726	Remote Similarity	NPD7515	Phase 2
0.6726	Remote Similarity	NPD5694	Approved
0.6724	Remote Similarity	NPD4755	Approved
0.6723	Remote Similarity	NPD5175	Approved
0.6723	Remote Similarity	NPD5174	Approved
0.6696	Remote Similarity	NPD5328	Approved
0.6696	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6637	Remote Similarity	NPD5692	Phase 3
0.661	Remote Similarity	NPD7640	Approved
0.661	Remote Similarity	NPD7639	Approved
0.661	Remote Similarity	NPD4700	Approved
0.6609	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7900	Approved
0.6579	Remote Similarity	NPD5281	Approved
0.6579	Remote Similarity	NPD5284	Approved
0.6579	Remote Similarity	NPD7983	Approved
0.6577	Remote Similarity	NPD5279	Phase 3
0.6577	Remote Similarity	NPD3618	Phase 1
0.6557	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6080	Approved
0.6549	Remote Similarity	NPD6904	Approved
0.6549	Remote Similarity	NPD6673	Approved
0.6544	Remote Similarity	NPD6845	Suspended
0.6541	Remote Similarity	NPD8074	Phase 3
0.6538	Remote Similarity	NPD6909	Approved
0.6538	Remote Similarity	NPD6908	Approved
0.6525	Remote Similarity	NPD4225	Approved
0.6504	Remote Similarity	NPD4730	Approved
0.6504	Remote Similarity	NPD4729	Approved
0.6491	Remote Similarity	NPD5207	Approved
0.6481	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4695	Discontinued
0.6475	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4754	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD6334	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD6333	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6423	Remote Similarity	NPD6614	Approved
0.6422	Remote Similarity	NPD5369	Approved
0.641	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4753	Phase 2
0.64	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5135	Approved
0.64	Remote Similarity	NPD5249	Phase 3
0.64	Remote Similarity	NPD5169	Approved
0.64	Remote Similarity	NPD5250	Approved
0.64	Remote Similarity	NPD5247	Approved
0.64	Remote Similarity	NPD5251	Approved
0.64	Remote Similarity	NPD5248	Approved
0.6396	Remote Similarity	NPD4786	Approved
0.6371	Remote Similarity	NPD5128	Approved
0.6371	Remote Similarity	NPD5168	Approved
0.6364	Remote Similarity	NPD3667	Approved
0.6356	Remote Similarity	NPD7839	Suspended
0.6355	Remote Similarity	NPD4756	Discovery
0.6349	Remote Similarity	NPD5217	Approved
0.6349	Remote Similarity	NPD5216	Approved
0.6349	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5215	Approved
0.6349	Remote Similarity	NPD5127	Approved
0.6341	Remote Similarity	NPD4768	Approved
0.6341	Remote Similarity	NPD4767	Approved
0.6339	Remote Similarity	NPD5363	Approved
0.6339	Remote Similarity	NPD1694	Approved
0.6316	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6110	Phase 1
0.6293	Remote Similarity	NPD7637	Suspended
0.6293	Remote Similarity	NPD5693	Phase 1
0.629	Remote Similarity	NPD6412	Phase 2
0.6288	Remote Similarity	NPD7503	Approved
0.6283	Remote Similarity	NPD4694	Approved
0.6283	Remote Similarity	NPD6098	Approved
0.6283	Remote Similarity	NPD5690	Phase 2
0.6283	Remote Similarity	NPD5786	Approved
0.6283	Remote Similarity	NPD5280	Approved
0.6277	Remote Similarity	NPD5956	Approved
0.6271	Remote Similarity	NPD5654	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3133	Approved
0.624	Remote Similarity	NPD6686	Approved
0.6239	Remote Similarity	NPD4202	Approved
0.6207	Remote Similarity	NPD5785	Approved
0.6204	Remote Similarity	NPD7319	Approved
0.6202	Remote Similarity	NPD5167	Approved
0.6195	Remote Similarity	NPD1696	Phase 3
0.6195	Remote Similarity	NPD5329	Approved
0.619	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8132	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