NPASS Compound

Structure

CID18785 OpenBabel06191715342D 21 22 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 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 6.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 4.4152 -4.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7242 -5.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7242 -1.7399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 20 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 3 1 1 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 6 0 0 0 14 16 2 0 0 0 0 17 21 1 0 0 0 0 18 21 2 0 0 0 0 19 21 2 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	294.292
LogP:	-0.328
LogD:	0.611
LogS:	-1.01
# Rotatable Bonds:	4
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.817
Synthetic Accessibility Score:	3.682
Fsp3:	0.5
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:	-4.993
MDCK Permeability:	9.249512004316784e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.257
20% Bioavailability (F20%):	0.817
30% Bioavailability (F30%):	0.113

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	90.47842407226562%
Volume Distribution (VD):	0.534
Pgp-substrate:	11.111525535583496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.805
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.528
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	1.727
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.202
Drug-inuced Liver Injury (DILI):	0.129
AMES Toxicity:	0.803
Rat Oral Acute Toxicity:	0.767
Maximum Recommended Daily Dose:	0.689
Skin Sensitization:	0.392
Carcinogencity:	0.883
Eye Corrosion:	0.006
Eye Irritation:	0.151
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC18785

Natural Product ID:	NPC18785
*Common Name:**	2-[(1S,2S)-1-Hydroxy-2,4,6-Trimethyl-3-Oxo-1,2-Dihydroinden-5-Yl]Ethyl Hydrogen Sulfate
IUPAC Name:	2-[(1S,2S)-1-hydroxy-2,4,6-trimethyl-3-oxo-1,2-dihydroinden-5-yl]ethyl hydrogen sulfate
Synonyms:	(2S,3S)-Sulfated pterosin C
Standard InCHIKey:	AJYKBYFVDNGNQI-ZANVPECISA-N
Standard InCHI:	InChI=1S/C14H18O6S/c1-7-6-11-12(14(16)9(3)13(11)15)8(2)10(7)4-5-20-21(17,18)19/h6,9,13,15H,4-5H2,1-3H3,(H,17,18,19)/t9-,13-/m0/s1
SMILES:	Cc1cc2[C@@H](O)[C@@H](C(=O)c2c(c1CCOS(=O)(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823116
PubChem CID:	54669844
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000027] Indanes [CHEMONTID:0001151] Indanones

*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
NPO13765	Acrostichum aureum	Species	Pteridaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21899268]
NPO13765	Acrostichum aureum	Species	Pteridaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22906240]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7010	Anthocleista procera	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14461	Vibrio fluvialis	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13868	Gnaphalium oligandrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11828	Mucor hiemalis	Species	Mucoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14357	Ixeris denticulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26896	Wulfenia orientalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13765	Acrostichum aureum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12686	Sideritis hirsuta	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	5
Others	2

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	46800.0	nM	PMID[544191]
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	23900.0	nM	PMID[544191]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	68800.0	nM	PMID[544191]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	100000.0	nM	PMID[544191]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	64400.0	nM	PMID[544191]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	6.8	%	PMID[544191]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	25.2	%	PMID[544191]

☑ 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 NPC18785 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	234
0.1-0.2	1150
0.2-0.3	2628
0.3-0.4	8041
0.4-0.5	14493
0.5-0.6	11970
0.6-0.7	3854
0.7-0.8	303
0.8-0.85	10
0.85-0.9	5
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9483	High Similarity	NPC133302
0.8644	High Similarity	NPC274839
0.8596	High Similarity	NPC83409
0.8596	High Similarity	NPC185763
0.8362	Intermediate Similarity	NPC112903
0.8209	Intermediate Similarity	NPC156393
0.8182	Intermediate Similarity	NPC476357
0.8151	Intermediate Similarity	NPC474057
0.8145	Intermediate Similarity	NPC472708
0.812	Intermediate Similarity	NPC37914
0.7881	Intermediate Similarity	NPC471133
0.7805	Intermediate Similarity	NPC196673
0.7797	Intermediate Similarity	NPC315794
0.7787	Intermediate Similarity	NPC471188
0.7769	Intermediate Similarity	NPC68756
0.7769	Intermediate Similarity	NPC152525
0.775	Intermediate Similarity	NPC211439
0.7744	Intermediate Similarity	NPC82712
0.7734	Intermediate Similarity	NPC472981
0.7731	Intermediate Similarity	NPC321670
0.768	Intermediate Similarity	NPC9274
0.7652	Intermediate Similarity	NPC472706
0.7642	Intermediate Similarity	NPC66208
0.7634	Intermediate Similarity	NPC234890
0.7634	Intermediate Similarity	NPC74507
0.7612	Intermediate Similarity	NPC262819
0.7603	Intermediate Similarity	NPC249811
0.76	Intermediate Similarity	NPC186933
0.7519	Intermediate Similarity	NPC470585
0.75	Intermediate Similarity	NPC318173
0.7481	Intermediate Similarity	NPC223351
0.7479	Intermediate Similarity	NPC304873
0.7479	Intermediate Similarity	NPC25458
0.7464	Intermediate Similarity	NPC474659
0.7464	Intermediate Similarity	NPC23894
0.7463	Intermediate Similarity	NPC115797
0.7463	Intermediate Similarity	NPC51448
0.7463	Intermediate Similarity	NPC472707
0.746	Intermediate Similarity	NPC474095
0.746	Intermediate Similarity	NPC215419
0.7444	Intermediate Similarity	NPC236405
0.7444	Intermediate Similarity	NPC131799
0.7444	Intermediate Similarity	NPC478107
0.7444	Intermediate Similarity	NPC470649
0.7426	Intermediate Similarity	NPC72915
0.7424	Intermediate Similarity	NPC85511
0.7424	Intermediate Similarity	NPC472704
0.7424	Intermediate Similarity	NPC228739
0.7422	Intermediate Similarity	NPC222968
0.7422	Intermediate Similarity	NPC80605
0.7422	Intermediate Similarity	NPC323440
0.7419	Intermediate Similarity	NPC265513
0.7417	Intermediate Similarity	NPC247976
0.7405	Intermediate Similarity	NPC269923
0.7405	Intermediate Similarity	NPC167323
0.7402	Intermediate Similarity	NPC135730
0.7398	Intermediate Similarity	NPC318327
0.7395	Intermediate Similarity	NPC469481
0.7395	Intermediate Similarity	NPC289117
0.7391	Intermediate Similarity	NPC203486
0.7391	Intermediate Similarity	NPC314048
0.7391	Intermediate Similarity	NPC310662
0.7388	Intermediate Similarity	NPC136342
0.7388	Intermediate Similarity	NPC81135
0.7388	Intermediate Similarity	NPC295202
0.7388	Intermediate Similarity	NPC227741
0.7388	Intermediate Similarity	NPC49647
0.7377	Intermediate Similarity	NPC100767
0.7373	Intermediate Similarity	NPC317280
0.7373	Intermediate Similarity	NPC329387
0.7368	Intermediate Similarity	NPC12818
0.736	Intermediate Similarity	NPC292834
0.7355	Intermediate Similarity	NPC249067
0.7348	Intermediate Similarity	NPC307174
0.7348	Intermediate Similarity	NPC65627
0.7348	Intermediate Similarity	NPC472703
0.7344	Intermediate Similarity	NPC212891
0.7344	Intermediate Similarity	NPC158157
0.7338	Intermediate Similarity	NPC477367
0.7338	Intermediate Similarity	NPC232888
0.7338	Intermediate Similarity	NPC474394
0.7328	Intermediate Similarity	NPC190971
0.7323	Intermediate Similarity	NPC93181
0.7323	Intermediate Similarity	NPC228936
0.7319	Intermediate Similarity	NPC242358
0.7319	Intermediate Similarity	NPC110609
0.7319	Intermediate Similarity	NPC246693
0.7311	Intermediate Similarity	NPC217621
0.7308	Intermediate Similarity	NPC476645
0.7302	Intermediate Similarity	NPC206414
0.7302	Intermediate Similarity	NPC287055
0.7302	Intermediate Similarity	NPC242957
0.7302	Intermediate Similarity	NPC13784
0.7302	Intermediate Similarity	NPC306977
0.7302	Intermediate Similarity	NPC470253
0.7299	Intermediate Similarity	NPC199253
0.7299	Intermediate Similarity	NPC136588
0.7299	Intermediate Similarity	NPC31799
0.7295	Intermediate Similarity	NPC471186
0.7286	Intermediate Similarity	NPC52523
0.7286	Intermediate Similarity	NPC217673
0.728	Intermediate Similarity	NPC133308
0.7279	Intermediate Similarity	NPC48248
0.7266	Intermediate Similarity	NPC477368
0.7259	Intermediate Similarity	NPC474106
0.7259	Intermediate Similarity	NPC472047
0.7259	Intermediate Similarity	NPC269598
0.7252	Intermediate Similarity	NPC238861
0.7252	Intermediate Similarity	NPC473662
0.7252	Intermediate Similarity	NPC289432
0.7252	Intermediate Similarity	NPC216297
0.7252	Intermediate Similarity	NPC988
0.7252	Intermediate Similarity	NPC77000
0.7252	Intermediate Similarity	NPC7151
0.7246	Intermediate Similarity	NPC233692
0.7244	Intermediate Similarity	NPC307651
0.7244	Intermediate Similarity	NPC474363
0.7244	Intermediate Similarity	NPC153053
0.7241	Intermediate Similarity	NPC314690
0.7239	Intermediate Similarity	NPC142956
0.7234	Intermediate Similarity	NPC315275
0.7231	Intermediate Similarity	NPC41567
0.7227	Intermediate Similarity	NPC229242
0.7226	Intermediate Similarity	NPC49272
0.7226	Intermediate Similarity	NPC474546
0.7226	Intermediate Similarity	NPC272946
0.7222	Intermediate Similarity	NPC477275
0.7222	Intermediate Similarity	NPC106519
0.7222	Intermediate Similarity	NPC91019
0.7222	Intermediate Similarity	NPC321852
0.7218	Intermediate Similarity	NPC282577
0.7214	Intermediate Similarity	NPC202225
0.7209	Intermediate Similarity	NPC477453
0.7206	Intermediate Similarity	NPC19432
0.7203	Intermediate Similarity	NPC242355
0.7197	Intermediate Similarity	NPC144547
0.7194	Intermediate Similarity	NPC477364
0.7194	Intermediate Similarity	NPC58685
0.7194	Intermediate Similarity	NPC70622
0.7185	Intermediate Similarity	NPC472592
0.7185	Intermediate Similarity	NPC167055
0.7185	Intermediate Similarity	NPC240744
0.7183	Intermediate Similarity	NPC305060
0.7183	Intermediate Similarity	NPC475957
0.7176	Intermediate Similarity	NPC473767
0.7174	Intermediate Similarity	NPC198305
0.7164	Intermediate Similarity	NPC275145
0.7164	Intermediate Similarity	NPC51079
0.7163	Intermediate Similarity	NPC309056
0.7154	Intermediate Similarity	NPC172483
0.7154	Intermediate Similarity	NPC105899
0.7153	Intermediate Similarity	NPC282923
0.7143	Intermediate Similarity	NPC329913
0.7143	Intermediate Similarity	NPC28836
0.7143	Intermediate Similarity	NPC477359
0.7143	Intermediate Similarity	NPC52407
0.7143	Intermediate Similarity	NPC311492
0.7143	Intermediate Similarity	NPC95126
0.7143	Intermediate Similarity	NPC260818
0.7143	Intermediate Similarity	NPC126516
0.7143	Intermediate Similarity	NPC115458
0.7143	Intermediate Similarity	NPC78307
0.7143	Intermediate Similarity	NPC369
0.7143	Intermediate Similarity	NPC293831
0.7143	Intermediate Similarity	NPC475002
0.7143	Intermediate Similarity	NPC253423
0.7132	Intermediate Similarity	NPC471930
0.7132	Intermediate Similarity	NPC169913
0.7132	Intermediate Similarity	NPC471929
0.7132	Intermediate Similarity	NPC306765
0.7132	Intermediate Similarity	NPC149691
0.7132	Intermediate Similarity	NPC161304
0.7132	Intermediate Similarity	NPC3224
0.7132	Intermediate Similarity	NPC471935
0.7131	Intermediate Similarity	NPC255676
0.7122	Intermediate Similarity	NPC85342
0.7122	Intermediate Similarity	NPC239358
0.7122	Intermediate Similarity	NPC41847
0.7122	Intermediate Similarity	NPC471851
0.7121	Intermediate Similarity	NPC234337
0.7121	Intermediate Similarity	NPC183339
0.7121	Intermediate Similarity	NPC285829
0.7121	Intermediate Similarity	NPC206778
0.7121	Intermediate Similarity	NPC133389
0.712	Intermediate Similarity	NPC83628
0.712	Intermediate Similarity	NPC265407
0.712	Intermediate Similarity	NPC85493
0.7113	Intermediate Similarity	NPC86524
0.7111	Intermediate Similarity	NPC199273
0.7111	Intermediate Similarity	NPC173978
0.7111	Intermediate Similarity	NPC117794
0.7111	Intermediate Similarity	NPC181334
0.7109	Intermediate Similarity	NPC477411
0.7109	Intermediate Similarity	NPC169616
0.7107	Intermediate Similarity	NPC282895
0.7101	Intermediate Similarity	NPC146647
0.7101	Intermediate Similarity	NPC34414
0.7101	Intermediate Similarity	NPC278928
0.7097	Intermediate Similarity	NPC130489
0.7097	Intermediate Similarity	NPC208676

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 NPC18785 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	874
0.2-0.3	1526
0.3-0.4	2895
0.4-0.5	2402
0.5-0.6	1043
0.6-0.7	179
0.7-0.8	15
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
0.7705	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD6085	Phase 2
0.7652	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1237	Approved
0.7323	Intermediate Similarity	NPD5951	Approved
0.7252	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1693	Approved
0.7101	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7009	Phase 2
0.7068	Intermediate Similarity	NPD3023	Approved
0.7068	Intermediate Similarity	NPD3026	Approved
0.7068	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7236	Approved
0.6992	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1930	Approved
0.6992	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3095	Discontinued
0.6992	Remote Similarity	NPD1929	Approved
0.6992	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7008	Discontinued
0.6934	Remote Similarity	NPD1470	Approved
0.6917	Remote Similarity	NPD3025	Approved
0.6917	Remote Similarity	NPD3024	Approved
0.6894	Remote Similarity	NPD7610	Discontinued
0.6889	Remote Similarity	NPD1201	Approved
0.6887	Remote Similarity	NPD7239	Suspended
0.6885	Remote Similarity	NPD2066	Phase 3
0.6866	Remote Similarity	NPD2932	Approved
0.6866	Remote Similarity	NPD3019	Approved
0.6855	Remote Similarity	NPD6647	Phase 2
0.685	Remote Similarity	NPD2182	Approved
0.6818	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9495	Approved
0.68	Remote Similarity	NPD164	Approved
0.6797	Remote Similarity	NPD1317	Discontinued
0.6795	Remote Similarity	NPD7057	Phase 3
0.6795	Remote Similarity	NPD7058	Phase 2
0.6794	Remote Similarity	NPD2629	Approved
0.6788	Remote Similarity	NPD182	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1089	Approved
0.678	Remote Similarity	NPD1090	Approved
0.678	Remote Similarity	NPD1086	Approved
0.6769	Remote Similarity	NPD7094	Approved
0.6769	Remote Similarity	NPD6858	Approved
0.6761	Remote Similarity	NPD6663	Approved
0.6759	Remote Similarity	NPD7305	Phase 1
0.6759	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3317	Approved
0.672	Remote Similarity	NPD5765	Approved
0.6716	Remote Similarity	NPD3091	Approved
0.6715	Remote Similarity	NPD4878	Approved
0.6714	Remote Similarity	NPD5736	Approved
0.6695	Remote Similarity	NPD800	Approved
0.6693	Remote Similarity	NPD6685	Approved
0.6692	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1088	Approved
0.6645	Remote Similarity	NPD6273	Approved
0.6643	Remote Similarity	NPD7961	Discontinued
0.6643	Remote Similarity	NPD5647	Approved
0.664	Remote Similarity	NPD1932	Approved
0.6639	Remote Similarity	NPD9256	Approved
0.6639	Remote Similarity	NPD9258	Approved
0.6619	Remote Similarity	NPD1876	Approved
0.6612	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7741	Discontinued
0.6589	Remote Similarity	NPD2329	Discontinued
0.6585	Remote Similarity	NPD3495	Discontinued
0.6557	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2346	Discontinued
0.6547	Remote Similarity	NPD5157	Phase 1
0.6547	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD5159	Phase 2
0.6529	Remote Similarity	NPD7631	Approved
0.6529	Remote Similarity	NPD1508	Approved
0.6525	Remote Similarity	NPD1087	Approved
0.6522	Remote Similarity	NPD3092	Approved
0.6516	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5404	Approved
0.6486	Remote Similarity	NPD5408	Approved
0.6486	Remote Similarity	NPD5406	Approved
0.6486	Remote Similarity	NPD5405	Approved
0.6471	Remote Similarity	NPD2534	Approved
0.6471	Remote Similarity	NPD2532	Approved
0.6471	Remote Similarity	NPD2533	Approved
0.6466	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD3094	Phase 2
0.6446	Remote Similarity	NPD7609	Phase 3
0.6443	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6002	Phase 3
0.6443	Remote Similarity	NPD6005	Phase 3
0.6443	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6004	Phase 3
0.6424	Remote Similarity	NPD7799	Discontinued
0.6419	Remote Similarity	NPD2799	Discontinued
0.6418	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7390	Discontinued
0.6403	Remote Similarity	NPD5618	Discontinued
0.6387	Remote Similarity	NPD650	Approved
0.6383	Remote Similarity	NPD1283	Approved
0.6382	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD5712	Approved
0.6371	Remote Similarity	NPD1843	Approved
0.6364	Remote Similarity	NPD7084	Phase 3
0.6357	Remote Similarity	NPD5048	Discontinued
0.6345	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD2652	Approved
0.6343	Remote Similarity	NPD2650	Approved
0.6341	Remote Similarity	NPD1202	Approved
0.6338	Remote Similarity	NPD1164	Approved
0.6324	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD9493	Approved
0.632	Remote Similarity	NPD1565	Approved
0.632	Remote Similarity	NPD1566	Phase 3
0.632	Remote Similarity	NPD1564	Approved
0.6319	Remote Similarity	NPD7055	Discontinued
0.6316	Remote Similarity	NPD7003	Approved
0.6316	Remote Similarity	NPD9508	Approved
0.6316	Remote Similarity	NPD6912	Phase 3
0.6311	Remote Similarity	NPD1239	Approved
0.6306	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1651	Approved
0.6304	Remote Similarity	NPD1245	Approved
0.6303	Remote Similarity	NPD9259	Approved
0.6303	Remote Similarity	NPD9257	Approved
0.6301	Remote Similarity	NPD7715	Approved
0.6301	Remote Similarity	NPD7714	Approved
0.6294	Remote Similarity	NPD2798	Approved
0.6288	Remote Similarity	NPD2067	Discontinued
0.6286	Remote Similarity	NPD6287	Discontinued
0.6284	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD6966	Discovery
0.6269	Remote Similarity	NPD5277	Phase 2
0.6267	Remote Similarity	NPD7137	Phase 2
0.626	Remote Similarity	NPD9267	Approved
0.626	Remote Similarity	NPD6406	Approved
0.626	Remote Similarity	NPD9263	Approved
0.626	Remote Similarity	NPD9264	Approved
0.6259	Remote Similarity	NPD2345	Approved
0.6259	Remote Similarity	NPD4059	Approved
0.6259	Remote Similarity	NPD5126	Approved
0.6259	Remote Similarity	NPD5125	Phase 3
0.6259	Remote Similarity	NPD4199	Phase 3
0.625	Remote Similarity	NPD5760	Phase 2
0.625	Remote Similarity	NPD5761	Phase 2
0.624	Remote Similarity	NPD1989	Approved
0.6234	Remote Similarity	NPD3300	Phase 2
0.6233	Remote Similarity	NPD3764	Approved
0.6233	Remote Similarity	NPD2313	Discontinued
0.6225	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7076	Approved
0.6222	Remote Similarity	NPD7077	Approved
0.6222	Remote Similarity	NPD6010	Discontinued
0.622	Remote Similarity	NPD1238	Approved
0.6214	Remote Similarity	NPD4879	Approved
0.6212	Remote Similarity	NPD74	Approved
0.6212	Remote Similarity	NPD9266	Approved
0.621	Remote Similarity	NPD845	Approved
0.6209	Remote Similarity	NPD4628	Phase 3
0.6203	Remote Similarity	NPD3226	Approved
0.6194	Remote Similarity	NPD8165	Discontinued
0.6186	Remote Similarity	NPD9491	Approved
0.6181	Remote Similarity	NPD4980	Approved
0.6176	Remote Similarity	NPD1246	Approved
0.6176	Remote Similarity	NPD4766	Approved
0.6174	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.617	Remote Similarity	NPD1281	Approved
0.6159	Remote Similarity	NPD2935	Discontinued
0.6154	Remote Similarity	NPD5909	Discontinued
0.6149	Remote Similarity	NPD4140	Approved
0.6148	Remote Similarity	NPD7635	Approved
0.6143	Remote Similarity	NPD1104	Approved
0.6143	Remote Similarity	NPD4626	Approved
0.6143	Remote Similarity	NPD5305	Approved
0.6143	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD5306	Approved
0.6138	Remote Similarity	NPD3661	Approved
0.6138	Remote Similarity	NPD3663	Approved
0.6138	Remote Similarity	NPD3662	Phase 3
0.6138	Remote Similarity	NPD3664	Approved
0.6127	Remote Similarity	NPD3972	Approved
0.6122	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1471	Phase 3
0.6118	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD5763	Approved
0.6118	Remote Similarity	NPD5762	Approved
0.6115	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD9545	Approved
0.6115	Remote Similarity	NPD4479	Discontinued
0.6111	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD7458	Discontinued
0.6093	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD9294	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