NPASS Compound

Structure

CID325054 OpenBabel06191716182D 34 38 0 0 1 0 0 0 0 0999 V2000 -0.3229 3.9210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7718 2.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2656 2.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2008 3.4289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2253 0.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6650 1.9653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9603 -2.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9164 4.3888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9150 1.4617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7609 3.9005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0713 3.9015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0702 0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3808 2.9265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2935 3.8187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5345 -0.4887 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9153 2.4377 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2259 2.4382 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3802 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5354 2.4387 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6894 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6897 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8440 -0.4882 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7604 2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0707 2.9260 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2256 1.4622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5351 1.4627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8674 4.6081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8437 -1.4882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7066 1.6827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5342 -1.4648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6902 2.9269 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 15 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 7 32 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 29 2 0 0 0 0 15 33 1 0 0 0 0 16 21 1 0 0 0 0 16 32 1 6 0 0 0 17 25 1 0 0 0 0 17 26 1 1 0 0 0 18 26 1 1 0 0 0 18 27 1 0 0 0 0 19 27 1 1 0 0 0 19 28 1 0 0 0 0 20 28 1 1 0 0 0 20 33 1 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 1 0 0 0 23 34 1 0 0 0 0 24 31 2 0 0 0 0 24 34 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.3
Volume:	494.894
LogP:	5.122
LogD:	3.993
LogS:	-4.593
# Rotatable Bonds:	3
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	5.057
Fsp3:	0.821
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:	-4.957
MDCK Permeability:	2.11358092201408e-05
Pgp-inhibitor:	0.939
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.877

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.624
Plasma Protein Binding (PPB):	93.77149963378906%
Volume Distribution (VD):	1.031
Pgp-substrate:	7.346928119659424%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.329
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.729
CYP2C9-inhibitor:	0.131
CYP2C9-substrate:	0.273
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	5.005
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.188
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.873
Maximum Recommended Daily Dose:	0.64
Skin Sensitization:	0.83
Carcinogencity:	0.139
Eye Corrosion:	0.004
Eye Irritation:	0.19
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC325054

Natural Product ID:	NPC325054
*Common Name:**	[(3R,4R,5As,5Br,7As,11As,11Br,13R,13As)-3-Hydroxy-4-Methoxy-5B,8,8,11A,13A-Pentamethyl-1-Oxo-4,5,5A,6,7,7A,9,10,11,11B,12,13-Dodecahydro-3H-Phenanthro[2,1-E][2]Benzofuran-13-Yl] Acetate
IUPAC Name:	[(3R,4R,5aS,5bR,7aS,11aS,11bR,13R,13aS)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydro-3H-phenanthro[2,1-e][2]benzofuran-13-yl] acetate
Synonyms:
Standard InCHIKey:	PWNLVHXPDDFBAP-YJFPDCRJSA-N
Standard InCHI:	InChI=1S/C28H42O6/c1-15(29)33-20-14-18-26(4)11-8-10-25(2,3)17(26)9-12-27(18,5)19-13-16(32-7)21-22(28(19,20)6)24(31)34-23(21)30/h16-20,23,30H,8-14H2,1-7H3/t16-,17+,18-,19+,20-,23-,26+,27-,28-/m1/s1
SMILES:	CO[C@@H]1C[C@@H]2[C@](C3=C1[C@H](O)OC3=O)(C)[C@H](OC(=O)C)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773897
PubChem CID:	54582289
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
NPO33664	Hyatella sp.	Species	n.a.	n.a.	n.a.	the coast of Soheuksan-do, Korea	n.a.	PMID[21341710]
NPO31085	Hyattella	Genus	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21341710]

☑ 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
MIC	6
Others	1

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	14800.0	nM	PMID[496700]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[496700]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	<	0.39	ug.mL-1	PMID[496700]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	25.0	ug.mL-1	PMID[496700]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	12.5	ug.mL-1	PMID[496700]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	1.56	ug.mL-1	PMID[496700]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[496700]

☑ 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 NPC325054 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	1556
0.2-0.3	4397
0.3-0.4	7872
0.4-0.5	12810
0.5-0.6	7072
0.6-0.7	5340
0.7-0.8	3217
0.8-0.85	143
0.85-0.9	23
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9703	High Similarity	NPC31522
0.9604	High Similarity	NPC90946
0.9604	High Similarity	NPC300614
0.9596	High Similarity	NPC471208
0.9495	High Similarity	NPC165250
0.9091	High Similarity	NPC224356
0.9091	High Similarity	NPC175351
0.9091	High Similarity	NPC151681
0.9091	High Similarity	NPC121402
0.9091	High Similarity	NPC132753
0.9057	High Similarity	NPC12046
0.9057	High Similarity	NPC194951
0.901	High Similarity	NPC471075
0.899	High Similarity	NPC472363
0.899	High Similarity	NPC472362
0.899	High Similarity	NPC154526
0.8972	High Similarity	NPC157441
0.875	High Similarity	NPC222161
0.8679	High Similarity	NPC189075
0.8679	High Similarity	NPC275539
0.8679	High Similarity	NPC476765
0.8654	High Similarity	NPC159533
0.86	High Similarity	NPC474554
0.8598	High Similarity	NPC476759
0.8598	High Similarity	NPC112457
0.8585	High Similarity	NPC110496
0.8558	High Similarity	NPC476081
0.8558	High Similarity	NPC295791
0.8544	High Similarity	NPC477971
0.8544	High Similarity	NPC477972
0.8544	High Similarity	NPC219285
0.8544	High Similarity	NPC161527
0.8544	High Similarity	NPC476767
0.8544	High Similarity	NPC228251
0.8544	High Similarity	NPC477968
0.8544	High Similarity	NPC20113
0.8519	High Similarity	NPC476766
0.85	High Similarity	NPC472640
0.85	High Similarity	NPC472641
0.8476	Intermediate Similarity	NPC478057
0.8462	Intermediate Similarity	NPC63249
0.8455	Intermediate Similarity	NPC25909
0.8431	Intermediate Similarity	NPC240673
0.8431	Intermediate Similarity	NPC17578
0.8416	Intermediate Similarity	NPC474555
0.8411	Intermediate Similarity	NPC187435
0.8411	Intermediate Similarity	NPC67321
0.8393	Intermediate Similarity	NPC473968
0.8393	Intermediate Similarity	NPC474483
0.8381	Intermediate Similarity	NPC58329
0.8381	Intermediate Similarity	NPC134077
0.8365	Intermediate Similarity	NPC477716
0.8365	Intermediate Similarity	NPC477721
0.8365	Intermediate Similarity	NPC324841
0.835	Intermediate Similarity	NPC477719
0.835	Intermediate Similarity	NPC477718
0.8349	Intermediate Similarity	NPC472666
0.8349	Intermediate Similarity	NPC235014
0.8333	Intermediate Similarity	NPC470312
0.8319	Intermediate Similarity	NPC291564
0.8318	Intermediate Similarity	NPC252296
0.8302	Intermediate Similarity	NPC95899
0.8302	Intermediate Similarity	NPC120321
0.8302	Intermediate Similarity	NPC254202
0.83	Intermediate Similarity	NPC472642
0.8286	Intermediate Similarity	NPC477717
0.8269	Intermediate Similarity	NPC325229
0.8269	Intermediate Similarity	NPC275086
0.8261	Intermediate Similarity	NPC476204
0.8261	Intermediate Similarity	NPC129434
0.8261	Intermediate Similarity	NPC170084
0.8252	Intermediate Similarity	NPC165632
0.8252	Intermediate Similarity	NPC234993
0.8252	Intermediate Similarity	NPC134072
0.8246	Intermediate Similarity	NPC477071
0.8246	Intermediate Similarity	NPC122971
0.8241	Intermediate Similarity	NPC184512
0.8241	Intermediate Similarity	NPC143609
0.8241	Intermediate Similarity	NPC475570
0.823	Intermediate Similarity	NPC13713
0.823	Intermediate Similarity	NPC477252
0.8224	Intermediate Similarity	NPC476764
0.8224	Intermediate Similarity	NPC476763
0.8218	Intermediate Similarity	NPC78594
0.8214	Intermediate Similarity	NPC472274
0.8214	Intermediate Similarity	NPC110861
0.8208	Intermediate Similarity	NPC469606
0.8208	Intermediate Similarity	NPC238397
0.8208	Intermediate Similarity	NPC273005
0.8208	Intermediate Similarity	NPC476769
0.8208	Intermediate Similarity	NPC137430
0.8208	Intermediate Similarity	NPC31058
0.8208	Intermediate Similarity	NPC471363
0.8198	Intermediate Similarity	NPC277769
0.8198	Intermediate Similarity	NPC269530
0.8198	Intermediate Similarity	NPC90952
0.8198	Intermediate Similarity	NPC477253
0.819	Intermediate Similarity	NPC47024
0.819	Intermediate Similarity	NPC251680
0.819	Intermediate Similarity	NPC477720
0.8174	Intermediate Similarity	NPC476150
0.8174	Intermediate Similarity	NPC476127
0.8173	Intermediate Similarity	NPC51499
0.8165	Intermediate Similarity	NPC392
0.8165	Intermediate Similarity	NPC177524
0.8165	Intermediate Similarity	NPC306265
0.8165	Intermediate Similarity	NPC219900
0.8165	Intermediate Similarity	NPC38948
0.8165	Intermediate Similarity	NPC285576
0.8165	Intermediate Similarity	NPC473483
0.8158	Intermediate Similarity	NPC276758
0.8158	Intermediate Similarity	NPC18233
0.8155	Intermediate Similarity	NPC135224
0.8155	Intermediate Similarity	NPC477969
0.8155	Intermediate Similarity	NPC471915
0.8148	Intermediate Similarity	NPC476760
0.8148	Intermediate Similarity	NPC476761
0.8148	Intermediate Similarity	NPC476762
0.8148	Intermediate Similarity	NPC469607
0.8148	Intermediate Similarity	NPC34768
0.8148	Intermediate Similarity	NPC111952
0.8142	Intermediate Similarity	NPC44170
0.8142	Intermediate Similarity	NPC471816
0.8142	Intermediate Similarity	NPC268954
0.8137	Intermediate Similarity	NPC472812
0.8137	Intermediate Similarity	NPC472303
0.8131	Intermediate Similarity	NPC8196
0.8131	Intermediate Similarity	NPC474822
0.8131	Intermediate Similarity	NPC7644
0.8131	Intermediate Similarity	NPC475889
0.8131	Intermediate Similarity	NPC127933
0.8131	Intermediate Similarity	NPC99266
0.8131	Intermediate Similarity	NPC134270
0.8131	Intermediate Similarity	NPC7613
0.8131	Intermediate Similarity	NPC120009
0.8131	Intermediate Similarity	NPC45897
0.8125	Intermediate Similarity	NPC264153
0.812	Intermediate Similarity	NPC27363
0.8113	Intermediate Similarity	NPC471412
0.8108	Intermediate Similarity	NPC191763
0.8095	Intermediate Similarity	NPC473154
0.8095	Intermediate Similarity	NPC216478
0.8095	Intermediate Similarity	NPC478056
0.8091	Intermediate Similarity	NPC472534
0.8091	Intermediate Similarity	NPC143706
0.8091	Intermediate Similarity	NPC206618
0.8091	Intermediate Similarity	NPC299590
0.8087	Intermediate Similarity	NPC475775
0.8087	Intermediate Similarity	NPC476529
0.8087	Intermediate Similarity	NPC232258
0.8083	Intermediate Similarity	NPC473593
0.8081	Intermediate Similarity	NPC474062
0.8077	Intermediate Similarity	NPC7124
0.8077	Intermediate Similarity	NPC94905
0.8077	Intermediate Similarity	NPC8954
0.8073	Intermediate Similarity	NPC293512
0.8073	Intermediate Similarity	NPC471205
0.807	Intermediate Similarity	NPC473405
0.807	Intermediate Similarity	NPC55296
0.8058	Intermediate Similarity	NPC104925
0.8058	Intermediate Similarity	NPC298973
0.8058	Intermediate Similarity	NPC189513
0.8058	Intermediate Similarity	NPC469697
0.8056	Intermediate Similarity	NPC470321
0.8056	Intermediate Similarity	NPC473207
0.8056	Intermediate Similarity	NPC81567
0.8056	Intermediate Similarity	NPC201880
0.8056	Intermediate Similarity	NPC264867
0.8039	Intermediate Similarity	NPC329842
0.8039	Intermediate Similarity	NPC289479
0.8039	Intermediate Similarity	NPC41239
0.8039	Intermediate Similarity	NPC472811
0.8037	Intermediate Similarity	NPC162973
0.8037	Intermediate Similarity	NPC121423
0.8036	Intermediate Similarity	NPC42658
0.8036	Intermediate Similarity	NPC4573
0.8036	Intermediate Similarity	NPC46388
0.8036	Intermediate Similarity	NPC470063
0.8036	Intermediate Similarity	NPC471967
0.8036	Intermediate Similarity	NPC37739
0.8036	Intermediate Similarity	NPC256798
0.8036	Intermediate Similarity	NPC128925
0.8036	Intermediate Similarity	NPC116794
0.8019	Intermediate Similarity	NPC476299
0.8019	Intermediate Similarity	NPC471413
0.8019	Intermediate Similarity	NPC473219
0.8019	Intermediate Similarity	NPC307954
0.8019	Intermediate Similarity	NPC474012
0.8019	Intermediate Similarity	NPC470761
0.8018	Intermediate Similarity	NPC119550
0.8018	Intermediate Similarity	NPC274507
0.8017	Intermediate Similarity	NPC48692
0.8017	Intermediate Similarity	NPC107338
0.8017	Intermediate Similarity	NPC268530
0.8017	Intermediate Similarity	NPC281840
0.8017	Intermediate Similarity	NPC109607
0.8017	Intermediate Similarity	NPC154491
0.8	Intermediate Similarity	NPC97867
0.8	Intermediate Similarity	NPC76266
0.8	Intermediate Similarity	NPC475709

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 NPC325054 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	1856
0.2-0.3	3630
0.3-0.4	2204
0.4-0.5	737
0.5-0.6	284
0.6-0.7	176
0.7-0.8	33
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.819	Intermediate Similarity	NPD7640	Approved
0.819	Intermediate Similarity	NPD7639	Approved
0.8165	Intermediate Similarity	NPD6686	Approved
0.8095	Intermediate Similarity	NPD7638	Approved
0.8091	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7632	Discontinued
0.8018	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD7507	Approved
0.7928	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD7319	Approved
0.7759	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7327	Approved
0.7692	Intermediate Similarity	NPD7328	Approved
0.7664	Intermediate Similarity	NPD7902	Approved
0.7647	Intermediate Similarity	NPD8033	Approved
0.7627	Intermediate Similarity	NPD7516	Approved
0.7607	Intermediate Similarity	NPD7115	Discovery
0.7589	Intermediate Similarity	NPD6412	Phase 2
0.7563	Intermediate Similarity	NPD8294	Approved
0.7563	Intermediate Similarity	NPD8377	Approved
0.7547	Intermediate Similarity	NPD7748	Approved
0.7524	Intermediate Similarity	NPD7515	Phase 2
0.7521	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8133	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.7431	Intermediate Similarity	NPD4225	Approved
0.7383	Intermediate Similarity	NPD7900	Approved
0.7383	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6399	Phase 3
0.728	Intermediate Similarity	NPD7736	Approved
0.7213	Intermediate Similarity	NPD7503	Approved
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
0.7196	Intermediate Similarity	NPD8034	Phase 2
0.7196	Intermediate Similarity	NPD8035	Phase 2
0.7193	Intermediate Similarity	NPD6402	Approved
0.7193	Intermediate Similarity	NPD6675	Approved
0.7193	Intermediate Similarity	NPD5739	Approved
0.7193	Intermediate Similarity	NPD7128	Approved
0.7184	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6373	Approved
0.7155	Intermediate Similarity	NPD6372	Approved
0.7119	Intermediate Similarity	NPD6882	Approved
0.7069	Intermediate Similarity	NPD7320	Approved
0.7069	Intermediate Similarity	NPD6881	Approved
0.7069	Intermediate Similarity	NPD6899	Approved
0.7063	Intermediate Similarity	NPD8293	Discontinued
0.7048	Intermediate Similarity	NPD3618	Phase 1
0.7043	Intermediate Similarity	NPD6008	Approved
0.7034	Intermediate Similarity	NPD6650	Approved
0.7034	Intermediate Similarity	NPD6649	Approved
0.7016	Intermediate Similarity	NPD6370	Approved
0.699	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5697	Approved
0.6983	Remote Similarity	NPD5701	Approved
0.6975	Remote Similarity	NPD6053	Discontinued
0.6952	Remote Similarity	NPD1694	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
0.6923	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7492	Approved
0.6891	Remote Similarity	NPD6869	Approved
0.6891	Remote Similarity	NPD6617	Approved
0.6891	Remote Similarity	NPD8130	Phase 1
0.6891	Remote Similarity	NPD6847	Approved
0.6885	Remote Similarity	NPD6009	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	NPD6059	Approved
0.6855	Remote Similarity	NPD6054	Approved
0.6852	Remote Similarity	NPD5328	Approved
0.685	Remote Similarity	NPD6616	Approved
0.6833	Remote Similarity	NPD8297	Approved
0.6825	Remote Similarity	NPD6067	Discontinued
0.6818	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5779	Approved
0.6797	Remote Similarity	NPD7078	Approved
0.6789	Remote Similarity	NPD46	Approved
0.6789	Remote Similarity	NPD6698	Approved
0.6783	Remote Similarity	NPD5211	Phase 2
0.678	Remote Similarity	NPD6011	Approved
0.6777	Remote Similarity	NPD4632	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
0.675	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7334	Approved
0.6729	Remote Similarity	NPD6684	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
0.672	Remote Similarity	NPD6319	Approved
0.6698	Remote Similarity	NPD4786	Approved
0.6697	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6637	Remote Similarity	NPD4697	Phase 3
0.6614	Remote Similarity	NPD5988	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
0.6577	Remote Similarity	NPD6411	Approved
0.6577	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD6117	Approved
0.6562	Remote Similarity	NPD7604	Phase 2
0.6549	Remote Similarity	NPD5695	Phase 3
0.6549	Remote Similarity	NPD6356	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
0.6535	Remote Similarity	NPD5983	Phase 2
0.6532	Remote Similarity	NPD6274	Approved
0.6522	Remote Similarity	NPD8029	Clinical (unspecified phase)
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	NPD5222	Approved
0.6491	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5221	Approved
0.6486	Remote Similarity	NPD5785	Approved
0.6466	Remote Similarity	NPD6648	Approved
0.6462	Remote Similarity	NPD6336	Discontinued
0.6441	Remote Similarity	NPD5174	Approved
0.6441	Remote Similarity	NPD5175	Approved
0.6435	Remote Similarity	NPD5173	Approved
0.6429	Remote Similarity	NPD6335	Approved
0.6429	Remote Similarity	NPD5693	Phase 1
0.6422	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5223	Approved
0.6406	Remote Similarity	NPD6909	Approved
0.6406	Remote Similarity	NPD6908	Approved
0.6404	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6868	Approved
0.6396	Remote Similarity	NPD4753	Phase 2
0.6396	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6101	Approved
0.6393	Remote Similarity	NPD4634	Approved
0.6387	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6033	Approved
0.6349	Remote Similarity	NPD6317	Approved
0.6343	Remote Similarity	NPD7260	Phase 2
0.6333	Remote Similarity	NPD4768	Approved
0.6333	Remote Similarity	NPD4767	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
0.6296	Remote Similarity	NPD6845	Suspended
0.6286	Remote Similarity	NPD3617	Approved
0.6283	Remote Similarity	NPD5281	Approved
0.6283	Remote Similarity	NPD5284	Approved
0.6281	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6921	Approved
0.6279	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4519	Discontinued
0.6273	Remote Similarity	NPD4623	Approved
0.6269	Remote Similarity	NPD6914	Discontinued
0.6261	Remote Similarity	NPD4629	Approved
0.6261	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD6051	Approved
0.625	Remote Similarity	NPD6673	Approved
0.625	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD6080	Approved
0.6239	Remote Similarity	NPD3668	Phase 3

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