NPASS Compound

Structure

NPC194847 OpenBabel07101718242D 32 35 0 0 1 0 0 0 0 0999 V2000 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5865 -1.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4135 -1.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -3.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1910 -2.5491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8090 -2.5491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -1.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5000 -1.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0000 -0.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 18 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 7 31 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 26 1 0 0 0 0 11 28 1 0 0 0 0 12 27 1 0 0 0 0 13 18 1 0 0 0 0 13 21 2 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 27 1 0 0 0 0 17 22 1 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 23 32 1 0 0 0 0 24 28 1 0 0 0 0 24 29 2 0 0 0 0 25 30 1 0 0 0 0 26 28 1 6 0 0 0 27 5 1 6 0 0 0 27 32 1 0 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.28
Volume:	477.96
LogP:	4.799
LogD:	3.584
LogS:	-5.493
# Rotatable Bonds:	4
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.582
Synthetic Accessibility Score:	4.904
Fsp3:	0.607
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.81
MDCK Permeability:	1.543088183098007e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.125
30% Bioavailability (F30%):	0.793

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.588
Plasma Protein Binding (PPB):	97.9621810913086%
Volume Distribution (VD):	1.651
Pgp-substrate:	1.8331907987594604%

ADMET: Metabolism

CYP1A2-inhibitor:	0.093
CYP1A2-substrate:	0.739
CYP2C19-inhibitor:	0.268
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.509
CYP2C9-substrate:	0.187
CYP2D6-inhibitor:	0.8
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.9

ADMET: Excretion

Clearance (CL):	9.62
Half-life (T1/2):	0.274

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.557
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.719
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.025
Carcinogencity:	0.913
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC194847

Natural Product ID:	NPC194847
*Common Name:**	(3As,7Ar)-5-(2-Hydroxy-2-Methylpropyl)-6-[[(2S)-6-Methoxy-2,8-Dimethylchromen-2-Yl]Methyl]-3A,7A-Dimethyl-1,2,3,7-Tetrahydroinden-4-One
IUPAC Name:	(3aS,7aR)-5-(2-hydroxy-2-methylpropyl)-6-[[(2S)-6-methoxy-2,8-dimethylchromen-2-yl]methyl]-3a,7a-dimethyl-1,2,3,7-tetrahydroinden-4-one
Synonyms:
Standard InCHIKey:	RHDGWMARJHUFRF-JCYYIGJDSA-N
Standard InCHI:	InChI=1S/C28H38O4/c1-18-13-21(31-7)14-19-9-12-27(5,32-23(18)19)16-20-15-26(4)10-8-11-28(26,6)24(29)22(20)17-25(2,3)30/h9,12-14,30H,8,10-11,15-17H2,1-7H3/t26-,27-,28-/m1/s1
SMILES:	Cc1cc(cc2C=C[C@](C)(CC3=C(CC(C)(C)O)C(=O)[C@@]4(C)CCC[C@]4(C)C3)Oc12)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL575389
PubChem CID:	25156146
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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
NPO27646	Cystoseira baccata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18980381]
NPO27646	Cystoseira baccata	Species	Sargassaceae	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
MIC	6
Others	2

Activity Type	# Activity
Organism	8
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6233	Organism	Sargassum muticum	Sargassum muticum	IC50	=	2.5	ug.mL-1	PMID[503165]
NPT6641	Organism	Ulva intestinalis	Ulva intestinalis	IC50	>	100.0	ug.mL-1	PMID[503165]
NPT2	Others	Unspecified		IC50	=	1.0	ug.mL-1	PMID[503165]
NPT6357	Organism	Pseudoalteromonas elyakovii	Pseudoalteromonas elyakovii	MIC	>	100.0	ug.mL-1	PMID[503165]
NPT6384	Organism	Vibrio aestuarianus	Vibrio aestuarianus	MIC	>	100.0	ug.mL-1	PMID[503165]
NPT6359	Organism	Polaribacter irgensii	Polaribacter irgensii	MIC	>	100.0	ug.mL-1	PMID[503165]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[503165]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[503165]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[503165]
NPT27	Others	Unspecified		LC50	>	100.0	ug.mL-1	PMID[503165]

☑ 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 NPC194847 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	301
0.1-0.2	1442
0.2-0.3	2673
0.3-0.4	7045
0.4-0.5	11884
0.5-0.6	5345
0.6-0.7	11691
0.7-0.8	2259
0.8-0.85	47
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC21797
0.9389	High Similarity	NPC251549
0.8686	High Similarity	NPC477210
0.8633	High Similarity	NPC98804
0.8529	High Similarity	NPC196621
0.8478	Intermediate Similarity	NPC470871
0.8444	Intermediate Similarity	NPC142087
0.8444	Intermediate Similarity	NPC95034
0.844	Intermediate Similarity	NPC265335
0.8429	Intermediate Similarity	NPC474610
0.8417	Intermediate Similarity	NPC27394
0.8406	Intermediate Similarity	NPC317601
0.8406	Intermediate Similarity	NPC329427
0.8403	Intermediate Similarity	NPC316691
0.8382	Intermediate Similarity	NPC201419
0.8346	Intermediate Similarity	NPC49441
0.8345	Intermediate Similarity	NPC471600
0.8333	Intermediate Similarity	NPC474143
0.8333	Intermediate Similarity	NPC474246
0.8333	Intermediate Similarity	NPC474154
0.8333	Intermediate Similarity	NPC258073
0.8321	Intermediate Similarity	NPC59654
0.8321	Intermediate Similarity	NPC206028
0.8273	Intermediate Similarity	NPC118253
0.8261	Intermediate Similarity	NPC475880
0.8252	Intermediate Similarity	NPC79372
0.8252	Intermediate Similarity	NPC76312
0.8239	Intermediate Similarity	NPC471542
0.8227	Intermediate Similarity	NPC281513
0.8227	Intermediate Similarity	NPC22222
0.8222	Intermediate Similarity	NPC276962
0.8222	Intermediate Similarity	NPC190086
0.8188	Intermediate Similarity	NPC271832
0.8182	Intermediate Similarity	NPC471449
0.8175	Intermediate Similarity	NPC477212
0.8175	Intermediate Similarity	NPC477211
0.8175	Intermediate Similarity	NPC319422
0.8175	Intermediate Similarity	NPC477214
0.8169	Intermediate Similarity	NPC64157
0.8169	Intermediate Similarity	NPC278832
0.8151	Intermediate Similarity	NPC474599
0.8129	Intermediate Similarity	NPC475102
0.8125	Intermediate Similarity	NPC475012
0.812	Intermediate Similarity	NPC168050
0.8112	Intermediate Similarity	NPC130976
0.8108	Intermediate Similarity	NPC60389
0.8099	Intermediate Similarity	NPC291119
0.8099	Intermediate Similarity	NPC281169
0.8095	Intermediate Similarity	NPC471451
0.8088	Intermediate Similarity	NPC147896
0.8088	Intermediate Similarity	NPC75432
0.8088	Intermediate Similarity	NPC474237
0.8082	Intermediate Similarity	NPC329493
0.8045	Intermediate Similarity	NPC51341
0.8045	Intermediate Similarity	NPC43435
0.8043	Intermediate Similarity	NPC298884
0.8029	Intermediate Similarity	NPC224657
0.8029	Intermediate Similarity	NPC477213
0.8015	Intermediate Similarity	NPC473718
0.8014	Intermediate Similarity	NPC312560
0.8	Intermediate Similarity	NPC7569
0.8	Intermediate Similarity	NPC475839
0.8	Intermediate Similarity	NPC470407
0.8	Intermediate Similarity	NPC476165
0.7987	Intermediate Similarity	NPC469507
0.7987	Intermediate Similarity	NPC472936
0.7987	Intermediate Similarity	NPC211565
0.7987	Intermediate Similarity	NPC472938
0.7987	Intermediate Similarity	NPC472937
0.7986	Intermediate Similarity	NPC301341
0.7986	Intermediate Similarity	NPC176590
0.7973	Intermediate Similarity	NPC169942
0.7972	Intermediate Similarity	NPC161856
0.7972	Intermediate Similarity	NPC51087
0.7956	Intermediate Similarity	NPC248557
0.7955	Intermediate Similarity	NPC69539
0.7945	Intermediate Similarity	NPC475063
0.7945	Intermediate Similarity	NPC475044
0.7943	Intermediate Similarity	NPC141549
0.7941	Intermediate Similarity	NPC302211
0.7939	Intermediate Similarity	NPC114144
0.7931	Intermediate Similarity	NPC475005
0.7931	Intermediate Similarity	NPC475104
0.7931	Intermediate Similarity	NPC474943
0.7926	Intermediate Similarity	NPC45663
0.7926	Intermediate Similarity	NPC212559
0.7926	Intermediate Similarity	NPC474175
0.7917	Intermediate Similarity	NPC471670
0.7914	Intermediate Similarity	NPC45537
0.7914	Intermediate Similarity	NPC156298
0.791	Intermediate Similarity	NPC32152
0.7902	Intermediate Similarity	NPC265793
0.7899	Intermediate Similarity	NPC320847
0.7895	Intermediate Similarity	NPC238176
0.7895	Intermediate Similarity	NPC187993
0.7891	Intermediate Similarity	NPC124365
0.7887	Intermediate Similarity	NPC474340
0.7881	Intermediate Similarity	NPC474107
0.7877	Intermediate Similarity	NPC475045
0.7877	Intermediate Similarity	NPC476191
0.7872	Intermediate Similarity	NPC278787
0.7868	Intermediate Similarity	NPC168707
0.7868	Intermediate Similarity	NPC48623
0.7862	Intermediate Similarity	NPC284184
0.7857	Intermediate Similarity	NPC477691
0.7857	Intermediate Similarity	NPC47288
0.7857	Intermediate Similarity	NPC81261
0.7852	Intermediate Similarity	NPC474131
0.7852	Intermediate Similarity	NPC232295
0.7852	Intermediate Similarity	NPC274085
0.7852	Intermediate Similarity	NPC71739
0.7852	Intermediate Similarity	NPC89664
0.7847	Intermediate Similarity	NPC22644
0.7847	Intermediate Similarity	NPC475011
0.7842	Intermediate Similarity	NPC128321
0.7832	Intermediate Similarity	NPC211352
0.7829	Intermediate Similarity	NPC472939
0.7829	Intermediate Similarity	NPC146014
0.7826	Intermediate Similarity	NPC61685
0.7821	Intermediate Similarity	NPC196448
0.7821	Intermediate Similarity	NPC44199
0.7817	Intermediate Similarity	NPC477412
0.7817	Intermediate Similarity	NPC205360
0.7817	Intermediate Similarity	NPC153019
0.7817	Intermediate Similarity	NPC239134
0.7815	Intermediate Similarity	NPC478163
0.781	Intermediate Similarity	NPC473464
0.781	Intermediate Similarity	NPC46586
0.781	Intermediate Similarity	NPC476332
0.781	Intermediate Similarity	NPC204535
0.7808	Intermediate Similarity	NPC475028
0.7808	Intermediate Similarity	NPC476025
0.7806	Intermediate Similarity	NPC3898
0.7801	Intermediate Similarity	NPC131684
0.7793	Intermediate Similarity	NPC115861
0.7792	Intermediate Similarity	NPC44606
0.7792	Intermediate Similarity	NPC477690
0.7786	Intermediate Similarity	NPC98372
0.7786	Intermediate Similarity	NPC471530
0.7786	Intermediate Similarity	NPC474920
0.7778	Intermediate Similarity	NPC231668
0.7771	Intermediate Similarity	NPC477692
0.7763	Intermediate Similarity	NPC146388
0.7762	Intermediate Similarity	NPC165612
0.7762	Intermediate Similarity	NPC289624
0.7762	Intermediate Similarity	NPC27578
0.7755	Intermediate Similarity	NPC477408
0.7754	Intermediate Similarity	NPC474130
0.7746	Intermediate Similarity	NPC470725
0.7746	Intermediate Similarity	NPC2989
0.7742	Intermediate Similarity	NPC178964
0.7742	Intermediate Similarity	NPC84721
0.7742	Intermediate Similarity	NPC135522
0.7742	Intermediate Similarity	NPC95842
0.7742	Intermediate Similarity	NPC280530
0.774	Intermediate Similarity	NPC477534
0.774	Intermediate Similarity	NPC118366
0.7733	Intermediate Similarity	NPC477409
0.7727	Intermediate Similarity	NPC48671
0.7724	Intermediate Similarity	NPC475029
0.7724	Intermediate Similarity	NPC476018
0.7721	Intermediate Similarity	NPC474874
0.7718	Intermediate Similarity	NPC201297
0.7718	Intermediate Similarity	NPC470273
0.7712	Intermediate Similarity	NPC266499
0.7712	Intermediate Similarity	NPC223988
0.771	Intermediate Similarity	NPC275627
0.7708	Intermediate Similarity	NPC263817
0.7708	Intermediate Similarity	NPC59459
0.7708	Intermediate Similarity	NPC477536
0.7707	Intermediate Similarity	NPC268602
0.7707	Intermediate Similarity	NPC67197
0.7704	Intermediate Similarity	NPC152159
0.7704	Intermediate Similarity	NPC139047
0.7703	Intermediate Similarity	NPC477535
0.7703	Intermediate Similarity	NPC155552
0.7698	Intermediate Similarity	NPC89630
0.7692	Intermediate Similarity	NPC164295
0.7692	Intermediate Similarity	NPC478161
0.7692	Intermediate Similarity	NPC279596
0.7692	Intermediate Similarity	NPC478159
0.7687	Intermediate Similarity	NPC98395
0.7687	Intermediate Similarity	NPC202260
0.7687	Intermediate Similarity	NPC148738
0.7687	Intermediate Similarity	NPC327612
0.7687	Intermediate Similarity	NPC73078
0.7687	Intermediate Similarity	NPC319870
0.7682	Intermediate Similarity	NPC212697
0.7681	Intermediate Similarity	NPC188997
0.7671	Intermediate Similarity	NPC475549
0.7671	Intermediate Similarity	NPC232996
0.7671	Intermediate Similarity	NPC472881
0.7667	Intermediate Similarity	NPC224884
0.7667	Intermediate Similarity	NPC53016
0.7667	Intermediate Similarity	NPC158871
0.7667	Intermediate Similarity	NPC209085
0.7664	Intermediate Similarity	NPC322569
0.7662	Intermediate Similarity	NPC321896
0.7662	Intermediate Similarity	NPC37348
0.7662	Intermediate Similarity	NPC119252

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 NPC194847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	901
0.2-0.3	1371
0.3-0.4	2460
0.4-0.5	2218
0.5-0.6	1290
0.6-0.7	547
0.7-0.8	82
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
0.8014	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD8032	Phase 2
0.7931	Intermediate Similarity	NPD2346	Discontinued
0.7879	Intermediate Similarity	NPD6671	Approved
0.7872	Intermediate Similarity	NPD2313	Discontinued
0.7826	Intermediate Similarity	NPD6696	Suspended
0.7794	Intermediate Similarity	NPD3496	Discontinued
0.777	Intermediate Similarity	NPD2797	Approved
0.7746	Intermediate Similarity	NPD3268	Approved
0.774	Intermediate Similarity	NPD6099	Approved
0.774	Intermediate Similarity	NPD6100	Approved
0.7671	Intermediate Similarity	NPD2799	Discontinued
0.7632	Intermediate Similarity	NPD6273	Approved
0.7619	Intermediate Similarity	NPD2935	Discontinued
0.7591	Intermediate Similarity	NPD1778	Approved
0.7591	Intermediate Similarity	NPD2932	Approved
0.7586	Intermediate Similarity	NPD6355	Discontinued
0.7568	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7095	Approved
0.7548	Intermediate Similarity	NPD7028	Phase 2
0.7535	Intermediate Similarity	NPD2861	Phase 2
0.7518	Intermediate Similarity	NPD3266	Approved
0.7518	Intermediate Similarity	NPD3267	Approved
0.7518	Intermediate Similarity	NPD1651	Approved
0.7517	Intermediate Similarity	NPD4140	Approved
0.7517	Intermediate Similarity	NPD2424	Discontinued
0.75	Intermediate Similarity	NPD5327	Phase 3
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3226	Approved
0.7482	Intermediate Similarity	NPD1611	Approved
0.7465	Intermediate Similarity	NPD2798	Approved
0.7464	Intermediate Similarity	NPD3019	Approved
0.7464	Intermediate Similarity	NPD4626	Approved
0.7463	Intermediate Similarity	NPD1241	Discontinued
0.7453	Intermediate Similarity	NPD8127	Discontinued
0.7452	Intermediate Similarity	NPD6844	Discontinued
0.7451	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6002	Phase 3
0.745	Intermediate Similarity	NPD6005	Phase 3
0.745	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6004	Phase 3
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7426	Intermediate Similarity	NPD7340	Approved
0.7417	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4110	Phase 3
0.7415	Intermediate Similarity	NPD6353	Approved
0.7391	Intermediate Similarity	NPD5691	Approved
0.7391	Intermediate Similarity	NPD5585	Approved
0.7379	Intermediate Similarity	NPD7985	Registered
0.7379	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2800	Approved
0.7351	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5735	Approved
0.7343	Intermediate Similarity	NPD4624	Approved
0.7333	Intermediate Similarity	NPD5762	Approved
0.7333	Intermediate Similarity	NPD5763	Approved
0.7333	Intermediate Similarity	NPD1398	Phase 1
0.7324	Intermediate Similarity	NPD8651	Approved
0.7324	Intermediate Similarity	NPD1283	Approved
0.7315	Intermediate Similarity	NPD7033	Discontinued
0.7305	Intermediate Similarity	NPD1608	Approved
0.7305	Intermediate Similarity	NPD3972	Approved
0.7303	Intermediate Similarity	NPD7003	Approved
0.7297	Intermediate Similarity	NPD6653	Approved
0.7296	Intermediate Similarity	NPD2801	Approved
0.7296	Intermediate Similarity	NPD7819	Suspended
0.7286	Intermediate Similarity	NPD3023	Approved
0.7286	Intermediate Similarity	NPD3026	Approved
0.7279	Intermediate Similarity	NPD4307	Phase 2
0.7266	Intermediate Similarity	NPD3025	Approved
0.7266	Intermediate Similarity	NPD3024	Approved
0.7261	Intermediate Similarity	NPD7458	Discontinued
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6798	Discontinued
0.7254	Intermediate Similarity	NPD4749	Approved
0.7246	Intermediate Similarity	NPD7644	Approved
0.7234	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7157	Approved
0.7222	Intermediate Similarity	NPD5647	Approved
0.7219	Intermediate Similarity	NPD2344	Approved
0.7214	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6663	Approved
0.7211	Intermediate Similarity	NPD6233	Phase 2
0.7203	Intermediate Similarity	NPD1876	Approved
0.7192	Intermediate Similarity	NPD4625	Phase 3
0.719	Intermediate Similarity	NPD8166	Discontinued
0.719	Intermediate Similarity	NPD3750	Approved
0.719	Intermediate Similarity	NPD4628	Phase 3
0.7188	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5494	Approved
0.7172	Intermediate Similarity	NPD5736	Approved
0.7162	Intermediate Similarity	NPD4060	Phase 1
0.7162	Intermediate Similarity	NPD2979	Phase 3
0.7153	Intermediate Similarity	NPD6362	Approved
0.7152	Intermediate Similarity	NPD4477	Approved
0.7152	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7097	Phase 1
0.7133	Intermediate Similarity	NPD4359	Approved
0.7123	Intermediate Similarity	NPD6832	Phase 2
0.7115	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD447	Suspended
0.7113	Intermediate Similarity	NPD1281	Approved
0.7113	Intermediate Similarity	NPD1535	Discovery
0.7105	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD17	Approved
0.7086	Intermediate Similarity	NPD3748	Approved
0.7083	Intermediate Similarity	NPD3225	Approved
0.7081	Intermediate Similarity	NPD5760	Phase 2
0.7081	Intermediate Similarity	NPD5761	Phase 2
0.7063	Intermediate Similarity	NPD9717	Approved
0.7063	Intermediate Similarity	NPD1481	Phase 2
0.7039	Intermediate Similarity	NPD6032	Approved
0.7039	Intermediate Similarity	NPD2796	Approved
0.7037	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5402	Approved
0.7032	Intermediate Similarity	NPD2309	Approved
0.7027	Intermediate Similarity	NPD411	Approved
0.7014	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2532	Approved
0.7006	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD4618	Approved
0.7	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4622	Approved
0.6993	Remote Similarity	NPD1471	Phase 3
0.6988	Remote Similarity	NPD7229	Phase 3
0.6987	Remote Similarity	NPD7236	Approved
0.6982	Remote Similarity	NPD5844	Phase 1
0.6981	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4097	Suspended
0.6954	Remote Similarity	NPD2157	Approved
0.6954	Remote Similarity	NPD8434	Phase 2
0.695	Remote Similarity	NPD1894	Discontinued
0.6947	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1511	Approved
0.694	Remote Similarity	NPD968	Approved
0.6939	Remote Similarity	NPD2237	Approved
0.6934	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6959	Discontinued
0.6918	Remote Similarity	NPD1470	Approved
0.6918	Remote Similarity	NPD1203	Approved
0.6914	Remote Similarity	NPD1934	Approved
0.6913	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5688	Approved
0.6908	Remote Similarity	NPD5689	Approved
0.6903	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6599	Discontinued
0.6894	Remote Similarity	NPD4380	Phase 2
0.6892	Remote Similarity	NPD2614	Approved
0.689	Remote Similarity	NPD7768	Phase 2
0.6887	Remote Similarity	NPD5124	Phase 1
0.6887	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7843	Approved
0.6884	Remote Similarity	NPD5535	Approved
0.6884	Remote Similarity	NPD7635	Approved
0.6883	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5536	Phase 2
0.6875	Remote Similarity	NPD1201	Approved
0.6871	Remote Similarity	NPD5929	Approved
0.6867	Remote Similarity	NPD4870	Approved
0.6866	Remote Similarity	NPD9697	Approved
0.6864	Remote Similarity	NPD7473	Discontinued
0.6863	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1510	Phase 2
0.686	Remote Similarity	NPD6765	Approved
0.686	Remote Similarity	NPD6764	Approved
0.6855	Remote Similarity	NPD1512	Approved
0.6855	Remote Similarity	NPD5049	Phase 3
0.6852	Remote Similarity	NPD7411	Suspended
0.6852	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7075	Discontinued
0.6842	Remote Similarity	NPD6651	Approved
0.6839	Remote Similarity	NPD4534	Discontinued
0.6839	Remote Similarity	NPD7974	Phase 3
0.6839	Remote Similarity	NPD1549	Phase 2
0.6839	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2684	Approved
0.6835	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2649	Approved
0.6832	Remote Similarity	NPD2651	Approved
0.6829	Remote Similarity	NPD3817	Phase 2
0.6829	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2230	Approved
0.6828	Remote Similarity	NPD2233	Approved
0.6828	Remote Similarity	NPD2232	Approved
0.6826	Remote Similarity	NPD1247	Approved
0.6821	Remote Similarity	NPD3620	Phase 2
0.6821	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2531	Phase 2
0.6818	Remote Similarity	NPD2438	Suspended

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