NPASS Compound

Structure

CID300614 OpenBabel06191716112D 30 34 0 0 1 0 0 0 0 0999 V2000 7.7347 -2.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2309 -2.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2052 -0.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6571 -1.9559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8882 -4.3678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8868 -1.4547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7287 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0471 -3.8829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0460 -0.9693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3638 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3646 -2.9125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5224 0.4864 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8870 -2.4261 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2057 -2.4266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3641 -0.9698 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5232 -2.4271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6813 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6816 -0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8399 0.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9708 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7281 -2.9110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0465 -2.9120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2055 -1.4552 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5230 -1.4557 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5221 1.4864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6574 -2.9273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8393 1.4859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7066 -1.6781 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 22 1 0 0 0 0 2 22 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 14 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 26 1 6 0 0 0 14 22 1 0 0 0 0 14 23 1 1 0 0 0 15 23 1 1 0 0 0 15 24 1 0 0 0 0 16 24 1 1 0 0 0 16 25 1 0 0 0 0 17 25 1 1 0 0 0 17 27 1 0 0 0 0 18 19 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 19 25 1 0 0 0 0 20 28 2 0 0 0 0 20 30 1 0 0 0 0 21 29 1 6 0 0 0 21 30 1 0 0 0 0 23 3 1 1 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.27
Volume:	436.852
LogP:	3.881
LogD:	3.084
LogS:	-4.554
# Rotatable Bonds:	0
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.475
Synthetic Accessibility Score:	5.026
Fsp3:	0.84
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.196
MDCK Permeability:	1.2482499187171925e-05
Pgp-inhibitor:	0.077
Pgp-substrate:	0.901
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.718
Plasma Protein Binding (PPB):	94.1604995727539%
Volume Distribution (VD):	1.636
Pgp-substrate:	9.50781536102295%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.219
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.626
CYP2C9-inhibitor:	0.152
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.276
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	7.251
Half-life (T1/2):	0.263

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.761
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.592
Carcinogencity:	0.197
Eye Corrosion:	0.004
Eye Irritation:	0.381
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC300614

Natural Product ID:	NPC300614
*Common Name:**	Hyrtiolide
IUPAC Name:	(1R,4R,5aS,5bR,7aS,11aS,11bR,13R,13aS)-1,4,13-trihydroxy-5b,8,8,11a,13a-pentamethyl-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-3-one
Synonyms:	Hyrtiolide
Standard InCHIKey:	GAQSWPYYPSDAAV-ZOBQAXMWSA-N
Standard InCHI:	InChI=1S/C25H38O5/c1-22(2)8-6-9-23(3)14(22)7-10-24(4)15(23)12-17(27)25(5)16(24)11-13(26)18-19(25)21(29)30-20(18)28/h13-17,21,26-27,29H,6-12H2,1-5H3/t13-,14+,15-,16+,17-,21-,23+,24-,25-/m1/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C[C@H]([C@@]2(C)[C@H]1C[C@H](C1=C2[C@H](O)OC1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078884
PubChem CID:	10693349
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO4034	Albizia adinocephala	Species	Fabaceae	Eukaryota	Stem bark and leaves	n.a.	n.a.	PMID[19299148]
NPO670	Hyrtios gumminae	Species	Thorectidae	Eukaryota	n.a.	Thai	n.a.	PMID[19788270]
NPO5186	Pimpinella aurea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO670	Hyrtios gumminae	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4034	Albizia adinocephala	Species	Fabaceae	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

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	12000.0	nM	PMID[472744]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	22000.0	nM	PMID[472744]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	26000.0	nM	PMID[472744]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	34000.0	nM	PMID[472744]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	57000.0	nM	PMID[472744]

☑ 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 NPC300614 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	250
0.1-0.2	1563
0.2-0.3	4383
0.3-0.4	7919
0.4-0.5	12869
0.5-0.6	7261
0.6-0.7	5221
0.7-0.8	3056
0.8-0.85	136
0.85-0.9	27
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC90946
0.99	High Similarity	NPC31522
0.9604	High Similarity	NPC325054
0.94	High Similarity	NPC471208
0.9394	High Similarity	NPC471075
0.9109	High Similarity	NPC165250
0.89	High Similarity	NPC175351
0.89	High Similarity	NPC121402
0.89	High Similarity	NPC132753
0.89	High Similarity	NPC151681
0.89	High Similarity	NPC224356
0.8857	High Similarity	NPC476765
0.88	High Similarity	NPC472363
0.88	High Similarity	NPC472362
0.88	High Similarity	NPC240673
0.88	High Similarity	NPC17578
0.88	High Similarity	NPC154526
0.8788	High Similarity	NPC474555
0.8774	High Similarity	NPC476759
0.8704	High Similarity	NPC194951
0.8704	High Similarity	NPC12046
0.8692	High Similarity	NPC476766
0.8654	High Similarity	NPC159533
0.8624	High Similarity	NPC157441
0.86	High Similarity	NPC474554
0.8585	High Similarity	NPC475570
0.8571	High Similarity	NPC222161
0.8559	High Similarity	NPC474483
0.8505	High Similarity	NPC473483
0.8476	Intermediate Similarity	NPC95899
0.8421	Intermediate Similarity	NPC170084
0.8421	Intermediate Similarity	NPC476204
0.8421	Intermediate Similarity	NPC129434
0.8396	Intermediate Similarity	NPC476764
0.8396	Intermediate Similarity	NPC476763
0.8381	Intermediate Similarity	NPC295791
0.8381	Intermediate Similarity	NPC476081
0.8378	Intermediate Similarity	NPC110861
0.8365	Intermediate Similarity	NPC161527
0.8365	Intermediate Similarity	NPC219285
0.8365	Intermediate Similarity	NPC476299
0.8365	Intermediate Similarity	NPC476767
0.8365	Intermediate Similarity	NPC474012
0.8365	Intermediate Similarity	NPC477972
0.8365	Intermediate Similarity	NPC228251
0.8365	Intermediate Similarity	NPC20113
0.8365	Intermediate Similarity	NPC477971
0.8365	Intermediate Similarity	NPC477968
0.8364	Intermediate Similarity	NPC90952
0.8364	Intermediate Similarity	NPC277769
0.835	Intermediate Similarity	NPC477719
0.835	Intermediate Similarity	NPC477718
0.835	Intermediate Similarity	NPC475709
0.8349	Intermediate Similarity	NPC472666
0.8349	Intermediate Similarity	NPC235014
0.8333	Intermediate Similarity	NPC476150
0.8333	Intermediate Similarity	NPC476127
0.8333	Intermediate Similarity	NPC275539
0.8333	Intermediate Similarity	NPC189075
0.8318	Intermediate Similarity	NPC476762
0.8318	Intermediate Similarity	NPC476760
0.8318	Intermediate Similarity	NPC476761
0.8317	Intermediate Similarity	NPC472640
0.8317	Intermediate Similarity	NPC472641
0.8304	Intermediate Similarity	NPC44170
0.8304	Intermediate Similarity	NPC268954
0.83	Intermediate Similarity	NPC472642
0.8286	Intermediate Similarity	NPC63249
0.8257	Intermediate Similarity	NPC112457
0.8252	Intermediate Similarity	NPC242848
0.8252	Intermediate Similarity	NPC234993
0.8252	Intermediate Similarity	NPC134072
0.8246	Intermediate Similarity	NPC232258
0.8241	Intermediate Similarity	NPC187435
0.8241	Intermediate Similarity	NPC67321
0.8241	Intermediate Similarity	NPC110496
0.823	Intermediate Similarity	NPC55296
0.823	Intermediate Similarity	NPC473968
0.8208	Intermediate Similarity	NPC134077
0.8208	Intermediate Similarity	NPC476890
0.8198	Intermediate Similarity	NPC42658
0.8198	Intermediate Similarity	NPC269530
0.8198	Intermediate Similarity	NPC4573
0.819	Intermediate Similarity	NPC477716
0.819	Intermediate Similarity	NPC117685
0.819	Intermediate Similarity	NPC324841
0.819	Intermediate Similarity	NPC477720
0.819	Intermediate Similarity	NPC477721
0.8174	Intermediate Similarity	NPC470312
0.8151	Intermediate Similarity	NPC311534
0.8148	Intermediate Similarity	NPC252296
0.8137	Intermediate Similarity	NPC472812
0.8137	Intermediate Similarity	NPC472303
0.8131	Intermediate Similarity	NPC120321
0.8131	Intermediate Similarity	NPC478057
0.8131	Intermediate Similarity	NPC476889
0.8125	Intermediate Similarity	NPC25909
0.8125	Intermediate Similarity	NPC264153
0.8113	Intermediate Similarity	NPC93744
0.8113	Intermediate Similarity	NPC477717
0.8113	Intermediate Similarity	NPC476888
0.8095	Intermediate Similarity	NPC275086
0.8095	Intermediate Similarity	NPC325229
0.8087	Intermediate Similarity	NPC122971
0.8083	Intermediate Similarity	NPC473593
0.8081	Intermediate Similarity	NPC474062
0.8077	Intermediate Similarity	NPC165632
0.8077	Intermediate Similarity	NPC7124
0.8073	Intermediate Similarity	NPC184512
0.807	Intermediate Similarity	NPC134430
0.8067	Intermediate Similarity	NPC469757
0.8067	Intermediate Similarity	NPC117702
0.8067	Intermediate Similarity	NPC471357
0.8067	Intermediate Similarity	NPC146456
0.8058	Intermediate Similarity	NPC104925
0.8058	Intermediate Similarity	NPC298973
0.8058	Intermediate Similarity	NPC469697
0.8053	Intermediate Similarity	NPC472274
0.8051	Intermediate Similarity	NPC318135
0.8051	Intermediate Similarity	NPC470922
0.8039	Intermediate Similarity	NPC329842
0.8039	Intermediate Similarity	NPC78594
0.8039	Intermediate Similarity	NPC73457
0.8039	Intermediate Similarity	NPC289479
0.8039	Intermediate Similarity	NPC472811
0.8037	Intermediate Similarity	NPC476769
0.8037	Intermediate Similarity	NPC471363
0.8037	Intermediate Similarity	NPC40918
0.8037	Intermediate Similarity	NPC58329
0.8037	Intermediate Similarity	NPC238397
0.8037	Intermediate Similarity	NPC471914
0.8036	Intermediate Similarity	NPC476163
0.8036	Intermediate Similarity	NPC477253
0.8019	Intermediate Similarity	NPC475156
0.8019	Intermediate Similarity	NPC251680
0.8019	Intermediate Similarity	NPC473576
0.8017	Intermediate Similarity	NPC268530
0.8017	Intermediate Similarity	NPC281840
0.8017	Intermediate Similarity	NPC154491
0.8	Intermediate Similarity	NPC177524
0.8	Intermediate Similarity	NPC392
0.8	Intermediate Similarity	NPC469845
0.8	Intermediate Similarity	NPC113448
0.8	Intermediate Similarity	NPC23020
0.8	Intermediate Similarity	NPC285576
0.8	Intermediate Similarity	NPC472269
0.8	Intermediate Similarity	NPC219900
0.8	Intermediate Similarity	NPC38948
0.8	Intermediate Similarity	NPC291564
0.8	Intermediate Similarity	NPC472268
0.8	Intermediate Similarity	NPC112492
0.8	Intermediate Similarity	NPC51499
0.8	Intermediate Similarity	NPC472270
0.8	Intermediate Similarity	NPC306265
0.7982	Intermediate Similarity	NPC111952
0.7982	Intermediate Similarity	NPC471816
0.7982	Intermediate Similarity	NPC34768
0.7981	Intermediate Similarity	NPC477969
0.7981	Intermediate Similarity	NPC471915
0.7981	Intermediate Similarity	NPC111273
0.7981	Intermediate Similarity	NPC135224
0.7981	Intermediate Similarity	NPC276110
0.7966	Intermediate Similarity	NPC27363
0.7965	Intermediate Similarity	NPC122056
0.7963	Intermediate Similarity	NPC112009
0.7963	Intermediate Similarity	NPC471938
0.7963	Intermediate Similarity	NPC134270
0.7963	Intermediate Similarity	NPC475889
0.7963	Intermediate Similarity	NPC7644
0.7963	Intermediate Similarity	NPC7613
0.7963	Intermediate Similarity	NPC45897
0.7963	Intermediate Similarity	NPC254202
0.7963	Intermediate Similarity	NPC120009
0.7963	Intermediate Similarity	NPC291154
0.7963	Intermediate Similarity	NPC474822
0.7963	Intermediate Similarity	NPC90177
0.7963	Intermediate Similarity	NPC127933
0.7961	Intermediate Similarity	NPC115021
0.7961	Intermediate Similarity	NPC139692
0.7951	Intermediate Similarity	NPC183816
0.7951	Intermediate Similarity	NPC324933
0.7951	Intermediate Similarity	NPC322904
0.7951	Intermediate Similarity	NPC475444
0.7951	Intermediate Similarity	NPC319719
0.7951	Intermediate Similarity	NPC233223
0.7951	Intermediate Similarity	NPC473679
0.7951	Intermediate Similarity	NPC231240
0.7951	Intermediate Similarity	NPC475177
0.7951	Intermediate Similarity	NPC196874
0.7949	Intermediate Similarity	NPC67569
0.7949	Intermediate Similarity	NPC4021
0.7949	Intermediate Similarity	NPC159456
0.7946	Intermediate Similarity	NPC474315
0.7946	Intermediate Similarity	NPC31839
0.7944	Intermediate Similarity	NPC471412
0.7941	Intermediate Similarity	NPC161638
0.7941	Intermediate Similarity	NPC78973
0.7941	Intermediate Similarity	NPC477782
0.7941	Intermediate Similarity	NPC281942
0.7941	Intermediate Similarity	NPC232426

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 NPC300614 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	1863
0.2-0.3	3585
0.3-0.4	2243
0.4-0.5	739
0.5-0.6	284
0.6-0.7	174
0.7-0.8	35
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8019	Intermediate Similarity	NPD7639	Approved
0.8019	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD6686	Approved
0.7934	Intermediate Similarity	NPD7319	Approved
0.7928	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7638	Approved
0.787	Intermediate Similarity	NPD7632	Discontinued
0.7833	Intermediate Similarity	NPD7507	Approved
0.7759	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7115	Discovery
0.7699	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4225	Approved
0.7547	Intermediate Similarity	NPD7748	Approved
0.7542	Intermediate Similarity	NPD7327	Approved
0.7542	Intermediate Similarity	NPD7328	Approved
0.7524	Intermediate Similarity	NPD7515	Phase 2
0.7521	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.7479	Intermediate Similarity	NPD7516	Approved
0.7434	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6412	Phase 2
0.7419	Intermediate Similarity	NPD7736	Approved
0.7417	Intermediate Similarity	NPD8377	Approved
0.7417	Intermediate Similarity	NPD8294	Approved
0.7355	Intermediate Similarity	NPD8379	Approved
0.7355	Intermediate Similarity	NPD8296	Approved
0.7355	Intermediate Similarity	NPD8378	Approved
0.7355	Intermediate Similarity	NPD8380	Approved
0.7355	Intermediate Similarity	NPD8335	Approved
0.735	Intermediate Similarity	NPD8133	Approved
0.7222	Intermediate Similarity	NPD7900	Approved
0.7222	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8517	Approved
0.7213	Intermediate Similarity	NPD8516	Approved
0.7213	Intermediate Similarity	NPD8513	Phase 3
0.7213	Intermediate Similarity	NPD8515	Approved
0.72	Intermediate Similarity	NPD8293	Discontinued
0.7193	Intermediate Similarity	NPD6675	Approved
0.7193	Intermediate Similarity	NPD7128	Approved
0.7193	Intermediate Similarity	NPD6402	Approved
0.7193	Intermediate Similarity	NPD5739	Approved
0.7184	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6370	Approved
0.713	Intermediate Similarity	NPD5779	Approved
0.713	Intermediate Similarity	NPD6399	Phase 3
0.713	Intermediate Similarity	NPD5778	Approved
0.7119	Intermediate Similarity	NPD6882	Approved
0.7073	Intermediate Similarity	NPD7503	Approved
0.7069	Intermediate Similarity	NPD7320	Approved
0.7069	Intermediate Similarity	NPD6881	Approved
0.7069	Intermediate Similarity	NPD6899	Approved
0.704	Intermediate Similarity	NPD7492	Approved
0.7037	Intermediate Similarity	NPD8035	Phase 2
0.7037	Intermediate Similarity	NPD8034	Phase 2
0.7009	Intermediate Similarity	NPD6372	Approved
0.7009	Intermediate Similarity	NPD6373	Approved
0.6992	Remote Similarity	NPD6059	Approved
0.6992	Remote Similarity	NPD6054	Approved
0.699	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6616	Approved
0.6983	Remote Similarity	NPD5697	Approved
0.6983	Remote Similarity	NPD5701	Approved
0.6952	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7290	Approved
0.6949	Remote Similarity	NPD7102	Approved
0.6949	Remote Similarity	NPD6883	Approved
0.6929	Remote Similarity	NPD7078	Approved
0.6923	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6869	Approved
0.6891	Remote Similarity	NPD6649	Approved
0.6891	Remote Similarity	NPD6617	Approved
0.6891	Remote Similarity	NPD6650	Approved
0.6891	Remote Similarity	NPD8130	Phase 1
0.6891	Remote Similarity	NPD6847	Approved
0.6887	Remote Similarity	NPD3618	Phase 1
0.6881	Remote Similarity	NPD7637	Suspended
0.6881	Remote Similarity	NPD6411	Approved
0.6875	Remote Similarity	NPD6084	Phase 2
0.6875	Remote Similarity	NPD6083	Phase 2
0.6864	Remote Similarity	NPD6013	Approved
0.6864	Remote Similarity	NPD6014	Approved
0.6864	Remote Similarity	NPD6012	Approved
0.6855	Remote Similarity	NPD6319	Approved
0.6852	Remote Similarity	NPD5328	Approved
0.6833	Remote Similarity	NPD6053	Discontinued
0.6833	Remote Similarity	NPD8297	Approved
0.68	Remote Similarity	NPD6015	Approved
0.68	Remote Similarity	NPD6016	Approved
0.6792	Remote Similarity	NPD1694	Approved
0.6783	Remote Similarity	NPD5211	Phase 2
0.678	Remote Similarity	NPD6011	Approved
0.6765	Remote Similarity	NPD6697	Approved
0.6765	Remote Similarity	NPD6115	Approved
0.6765	Remote Similarity	NPD6118	Approved
0.6765	Remote Similarity	NPD6114	Approved
0.6752	Remote Similarity	NPD6008	Approved
0.675	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6009	Approved
0.6746	Remote Similarity	NPD5988	Approved
0.6729	Remote Similarity	NPD6684	Approved
0.6729	Remote Similarity	NPD7334	Approved
0.6729	Remote Similarity	NPD6409	Approved
0.6729	Remote Similarity	NPD7521	Approved
0.6729	Remote Similarity	NPD5330	Approved
0.6729	Remote Similarity	NPD7146	Approved
0.6727	Remote Similarity	NPD6079	Approved
0.6726	Remote Similarity	NPD4755	Approved
0.6698	Remote Similarity	NPD4786	Approved
0.6697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6101	Approved
0.6693	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD6371	Approved
0.6639	Remote Similarity	NPD4632	Approved
0.6636	Remote Similarity	NPD5785	Approved
0.6636	Remote Similarity	NPD6698	Approved
0.6636	Remote Similarity	NPD46	Approved
0.6609	Remote Similarity	NPD4700	Approved
0.6609	Remote Similarity	NPD5285	Approved
0.6609	Remote Similarity	NPD4696	Approved
0.6609	Remote Similarity	NPD5286	Approved
0.6606	Remote Similarity	NPD6672	Approved
0.6606	Remote Similarity	NPD6903	Approved
0.6606	Remote Similarity	NPD5737	Approved
0.6574	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6117	Approved
0.6552	Remote Similarity	NPD5344	Discontinued
0.6549	Remote Similarity	NPD5695	Phase 3
0.6549	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3665	Phase 1
0.6542	Remote Similarity	NPD3133	Approved
0.6542	Remote Similarity	NPD3666	Approved
0.6538	Remote Similarity	NPD8074	Phase 3
0.6538	Remote Similarity	NPD7645	Phase 2
0.6532	Remote Similarity	NPD6274	Approved
0.6522	Remote Similarity	NPD5696	Approved
0.6514	Remote Similarity	NPD3573	Approved
0.6508	Remote Similarity	NPD7100	Approved
0.6508	Remote Similarity	NPD7101	Approved
0.6496	Remote Similarity	NPD5226	Approved
0.6496	Remote Similarity	NPD5225	Approved
0.6496	Remote Similarity	NPD5224	Approved
0.6496	Remote Similarity	NPD4633	Approved
0.6491	Remote Similarity	NPD4697	Phase 3
0.6491	Remote Similarity	NPD5222	Approved
0.6491	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5221	Approved
0.6489	Remote Similarity	NPD6033	Approved
0.6475	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5174	Approved
0.6441	Remote Similarity	NPD5175	Approved
0.6435	Remote Similarity	NPD5173	Approved
0.6434	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD5693	Phase 1
0.6429	Remote Similarity	NPD6335	Approved
0.641	Remote Similarity	NPD5223	Approved
0.6406	Remote Similarity	NPD6909	Approved
0.6406	Remote Similarity	NPD6908	Approved
0.6406	Remote Similarity	NPD5983	Phase 2
0.6404	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6868	Approved
0.6396	Remote Similarity	NPD4753	Phase 2
0.6391	Remote Similarity	NPD6914	Discontinued
0.6373	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6317	Approved
0.6348	Remote Similarity	NPD7839	Suspended
0.6336	Remote Similarity	NPD6336	Discontinued
0.6333	Remote Similarity	NPD4768	Approved
0.6333	Remote Similarity	NPD4767	Approved
0.6325	Remote Similarity	NPD6648	Approved
0.6321	Remote Similarity	NPD7525	Registered
0.6303	Remote Similarity	NPD4754	Approved
0.6299	Remote Similarity	NPD6314	Approved
0.6299	Remote Similarity	NPD6313	Approved
0.6286	Remote Similarity	NPD3617	Approved
0.6283	Remote Similarity	NPD7983	Approved
0.6281	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6921	Approved
0.6273	Remote Similarity	NPD4519	Discontinued
0.6273	Remote Similarity	NPD4623	Approved
0.625	Remote Similarity	NPD6051	Approved
0.625	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6673	Approved
0.625	Remote Similarity	NPD6080	Approved
0.6239	Remote Similarity	NPD3668	Phase 3
0.6239	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5128	Approved
0.623	Remote Similarity	NPD4730	Approved
0.623	Remote Similarity	NPD4729	Approved
0.6207	Remote Similarity	NPD7614	Phase 1

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