NPASS Compound

Structure

NPC120539 OpenBabel07101718312D 31 35 0 0 1 0 0 0 0 0999 V2000 1.3685 1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7350 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2350 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6994 1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8690 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7350 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0084 2.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -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 -0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 18 1 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 30 1 0 0 0 0 16 28 2 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 29 1 1 0 0 0 19 24 1 0 0 0 0 19 25 1 1 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 23 1 0 0 0 0 22 27 1 1 0 0 0 23 30 1 0 0 0 0 23 31 1 6 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 27 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.31
Volume:	462.654
LogP:	4.891
LogD:	4.274
LogS:	-4.587
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	4.921
Fsp3:	0.889
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:	-4.773
MDCK Permeability:	2.3665852495469153e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.733
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.423
Plasma Protein Binding (PPB):	88.52105712890625%
Volume Distribution (VD):	1.742
Pgp-substrate:	9.982733726501465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.199
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.76
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.706
CYP3A4-substrate:	0.523

ADMET: Excretion

Clearance (CL):	7.275
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.678
Human Hepatotoxicity (H-HT):	0.586
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.829
Carcinogencity:	0.929
Eye Corrosion:	0.627
Eye Irritation:	0.168
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC120539

Natural Product ID:	NPC120539
*Common Name:**	[(1S,4S,5As,5Br,7As,11As,11Br,13As,13Br)-4-Hydroxy-5B,8,8,11A,13A-Pentamethyl-1,4,5,5A,6,7,7A,9,10,11,11B,12,13,13B-Tetradecahydrophenanthro[1,2-G][2]Benzofuran-1-Yl] Acetate
IUPAC Name:	[(1S,4S,5aS,5bR,7aS,11aS,11bR,13aS,13bR)-4-hydroxy-5b,8,8,11a,13a-pentamethyl-1,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[1,2-g][2]benzofuran-1-yl] acetate
Synonyms:
Standard InCHIKey:	FQJRSISTDYPNPR-ARCYHYOLSA-N
Standard InCHI:	InChI=1S/C27H42O4/c1-16(28)31-23-22-17(15-30-23)18(29)14-21-26(5)12-8-19-24(2,3)10-7-11-25(19,4)20(26)9-13-27(21,22)6/h15,18-23,29H,7-14H2,1-6H3/t18-,19-,20+,21-,22+,23-,25-,26+,27-/m0/s1
SMILES:	CC(=O)O[C@@H]1OC=C2[C@H]1[C@@]1(C)CC[C@H]3[C@@]([C@@H]1C[C@@H]2O)(C)CC[C@@H]1[C@]3(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL572476
PubChem CID:	25158708
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
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]

☑ 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	1
MIC	6
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	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	=	5.8	ug.mL-1	PMID[456091]
NPT4391	Individual Protein	Isocitrate lyase	Magnaporthe oryzae (strain 70-15 / FGSC 8958) (Rice blast fungus)(Pyricularia oryzae)	IC50	>	100.0	ug.mL-1	PMID[456091]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[456091]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.12	ug.mL-1	PMID[456091]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[456091]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[456091]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	12.5	ug.mL-1	PMID[456091]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[456091]

☑ 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 NPC120539 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	229
0.1-0.2	1835
0.2-0.3	5736
0.3-0.4	15161
0.4-0.5	8717
0.5-0.6	5441
0.6-0.7	4351
0.7-0.8	1212
0.8-0.85	9
0.85-0.9	2
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC246860
0.9231	High Similarity	NPC97867
0.9195	High Similarity	NPC144069
0.8791	High Similarity	NPC163902
0.8511	High Similarity	NPC164750
0.8333	Intermediate Similarity	NPC168231
0.8152	Intermediate Similarity	NPC263079
0.8061	Intermediate Similarity	NPC146188
0.8061	Intermediate Similarity	NPC219285
0.8061	Intermediate Similarity	NPC161527
0.8061	Intermediate Similarity	NPC477971
0.8061	Intermediate Similarity	NPC228251
0.8061	Intermediate Similarity	NPC477972
0.8061	Intermediate Similarity	NPC477968
0.8061	Intermediate Similarity	NPC20113
0.8043	Intermediate Similarity	NPC288952
0.8022	Intermediate Similarity	NPC164424
0.802	Intermediate Similarity	NPC165405
0.8	Intermediate Similarity	NPC5280
0.7979	Intermediate Similarity	NPC471371
0.7979	Intermediate Similarity	NPC471370
0.7957	Intermediate Similarity	NPC160304
0.7941	Intermediate Similarity	NPC470169
0.7941	Intermediate Similarity	NPC470170
0.7917	Intermediate Similarity	NPC469697
0.7895	Intermediate Similarity	NPC329842
0.7895	Intermediate Similarity	NPC472811
0.7882	Intermediate Similarity	NPC12680
0.7879	Intermediate Similarity	NPC477716
0.7879	Intermediate Similarity	NPC477721
0.7857	Intermediate Similarity	NPC471770
0.7857	Intermediate Similarity	NPC477719
0.7857	Intermediate Similarity	NPC278939
0.7857	Intermediate Similarity	NPC477718
0.7857	Intermediate Similarity	NPC473555
0.7843	Intermediate Similarity	NPC470055
0.7843	Intermediate Similarity	NPC470056
0.7812	Intermediate Similarity	NPC26046
0.7812	Intermediate Similarity	NPC472812
0.7802	Intermediate Similarity	NPC474284
0.7802	Intermediate Similarity	NPC474346
0.7802	Intermediate Similarity	NPC474253
0.7802	Intermediate Similarity	NPC213737
0.7802	Intermediate Similarity	NPC475820
0.78	Intermediate Similarity	NPC477717
0.7789	Intermediate Similarity	NPC123252
0.7789	Intermediate Similarity	NPC194485
0.7789	Intermediate Similarity	NPC219937
0.7789	Intermediate Similarity	NPC469403
0.7789	Intermediate Similarity	NPC53890
0.7778	Intermediate Similarity	NPC157739
0.7778	Intermediate Similarity	NPC474092
0.7767	Intermediate Similarity	NPC470166
0.7766	Intermediate Similarity	NPC16377
0.7755	Intermediate Similarity	NPC299654
0.7755	Intermediate Similarity	NPC8954
0.7755	Intermediate Similarity	NPC94905
0.7755	Intermediate Similarity	NPC162346
0.7742	Intermediate Similarity	NPC471369
0.7742	Intermediate Similarity	NPC137306
0.7742	Intermediate Similarity	NPC187545
0.7742	Intermediate Similarity	NPC84121
0.7732	Intermediate Similarity	NPC298973
0.7732	Intermediate Similarity	NPC470255
0.7732	Intermediate Similarity	NPC324078
0.7732	Intermediate Similarity	NPC104925
0.7732	Intermediate Similarity	NPC211238
0.7723	Intermediate Similarity	NPC31085
0.7717	Intermediate Similarity	NPC299963
0.7717	Intermediate Similarity	NPC471367
0.77	Intermediate Similarity	NPC471247
0.77	Intermediate Similarity	NPC324841
0.77	Intermediate Similarity	NPC317019
0.7692	Intermediate Similarity	NPC472504
0.7692	Intermediate Similarity	NPC2096
0.7692	Intermediate Similarity	NPC208912
0.7684	Intermediate Similarity	NPC293044
0.7667	Intermediate Similarity	NPC206735
0.7667	Intermediate Similarity	NPC304194
0.766	Intermediate Similarity	NPC33768
0.7653	Intermediate Similarity	NPC472441
0.7653	Intermediate Similarity	NPC286612
0.7653	Intermediate Similarity	NPC477969
0.7653	Intermediate Similarity	NPC477970
0.7653	Intermediate Similarity	NPC135224
0.7653	Intermediate Similarity	NPC100892
0.7653	Intermediate Similarity	NPC230347
0.7653	Intermediate Similarity	NPC275310
0.7647	Intermediate Similarity	NPC471467
0.7634	Intermediate Similarity	NPC191965
0.7629	Intermediate Similarity	NPC12297
0.7624	Intermediate Similarity	NPC144486
0.7624	Intermediate Similarity	NPC121072
0.7624	Intermediate Similarity	NPC21064
0.7604	Intermediate Similarity	NPC471433
0.7604	Intermediate Similarity	NPC78973
0.7604	Intermediate Similarity	NPC471432
0.76	Intermediate Similarity	NPC473154
0.76	Intermediate Similarity	NPC325229
0.76	Intermediate Similarity	NPC469725
0.76	Intermediate Similarity	NPC477928
0.76	Intermediate Similarity	NPC275086
0.7579	Intermediate Similarity	NPC319030
0.7579	Intermediate Similarity	NPC472810
0.7579	Intermediate Similarity	NPC474629
0.7579	Intermediate Similarity	NPC472809
0.7579	Intermediate Similarity	NPC4309
0.7573	Intermediate Similarity	NPC173583
0.7573	Intermediate Similarity	NPC470768
0.7556	Intermediate Similarity	NPC305835
0.7553	Intermediate Similarity	NPC173917
0.7553	Intermediate Similarity	NPC471368
0.7553	Intermediate Similarity	NPC474970
0.7553	Intermediate Similarity	NPC2783
0.7553	Intermediate Similarity	NPC12774
0.7551	Intermediate Similarity	NPC189513
0.7551	Intermediate Similarity	NPC3359
0.7549	Intermediate Similarity	NPC177701
0.7549	Intermediate Similarity	NPC470571
0.7549	Intermediate Similarity	NPC154452
0.7528	Intermediate Similarity	NPC212241
0.7528	Intermediate Similarity	NPC248830
0.7528	Intermediate Similarity	NPC119355
0.7528	Intermediate Similarity	NPC84868
0.7527	Intermediate Similarity	NPC319238
0.7527	Intermediate Similarity	NPC102048
0.7526	Intermediate Similarity	NPC160506
0.7526	Intermediate Similarity	NPC48463
0.7526	Intermediate Similarity	NPC130840
0.7525	Intermediate Similarity	NPC91497
0.7524	Intermediate Similarity	NPC300614
0.7524	Intermediate Similarity	NPC88744
0.7524	Intermediate Similarity	NPC325054
0.7524	Intermediate Similarity	NPC90946
0.75	Intermediate Similarity	NPC51499
0.75	Intermediate Similarity	NPC470763
0.75	Intermediate Similarity	NPC470425
0.75	Intermediate Similarity	NPC470734
0.75	Intermediate Similarity	NPC98112
0.75	Intermediate Similarity	NPC473199
0.75	Intermediate Similarity	NPC470767
0.75	Intermediate Similarity	NPC158347
0.75	Intermediate Similarity	NPC144075
0.7476	Intermediate Similarity	NPC281378
0.7476	Intermediate Similarity	NPC120009
0.7476	Intermediate Similarity	NPC471208
0.7476	Intermediate Similarity	NPC473198
0.7476	Intermediate Similarity	NPC45897
0.7475	Intermediate Similarity	NPC241047
0.7474	Intermediate Similarity	NPC269360
0.7474	Intermediate Similarity	NPC264005
0.7453	Intermediate Similarity	NPC91583
0.7453	Intermediate Similarity	NPC206618
0.7453	Intermediate Similarity	NPC240125
0.7453	Intermediate Similarity	NPC31522
0.7453	Intermediate Similarity	NPC51947
0.7453	Intermediate Similarity	NPC473844
0.7451	Intermediate Similarity	NPC470168
0.7449	Intermediate Similarity	NPC474835
0.7449	Intermediate Similarity	NPC475061
0.7449	Intermediate Similarity	NPC287118
0.7449	Intermediate Similarity	NPC473690
0.7449	Intermediate Similarity	NPC53555
0.7449	Intermediate Similarity	NPC471902
0.7447	Intermediate Similarity	NPC264317
0.7447	Intermediate Similarity	NPC294438
0.7444	Intermediate Similarity	NPC301707
0.7431	Intermediate Similarity	NPC472274
0.7431	Intermediate Similarity	NPC469821
0.7429	Intermediate Similarity	NPC473538
0.7429	Intermediate Similarity	NPC234160
0.7429	Intermediate Similarity	NPC283849
0.7429	Intermediate Similarity	NPC475074
0.7426	Intermediate Similarity	NPC474440
0.7423	Intermediate Similarity	NPC474728
0.7423	Intermediate Similarity	NPC10274
0.7419	Intermediate Similarity	NPC132386
0.7419	Intermediate Similarity	NPC471037
0.7419	Intermediate Similarity	NPC473742
0.7416	Intermediate Similarity	NPC14112
0.7416	Intermediate Similarity	NPC38141
0.7416	Intermediate Similarity	NPC86305
0.7404	Intermediate Similarity	NPC470062
0.7404	Intermediate Similarity	NPC470060
0.7404	Intermediate Similarity	NPC470064
0.7404	Intermediate Similarity	NPC470058
0.7404	Intermediate Similarity	NPC470043
0.7404	Intermediate Similarity	NPC222161
0.7404	Intermediate Similarity	NPC470057
0.7404	Intermediate Similarity	NPC470059
0.7404	Intermediate Similarity	NPC470061
0.74	Intermediate Similarity	NPC111834
0.74	Intermediate Similarity	NPC327179
0.74	Intermediate Similarity	NPC253115
0.74	Intermediate Similarity	NPC317573
0.74	Intermediate Similarity	NPC472989
0.74	Intermediate Similarity	NPC306797
0.74	Intermediate Similarity	NPC116457
0.74	Intermediate Similarity	NPC304899
0.74	Intermediate Similarity	NPC169270

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 NPC120539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	2134
0.2-0.3	4021
0.3-0.4	1980
0.4-0.5	438
0.5-0.6	304
0.6-0.7	53
0.7-0.8	13
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
0.7526	Intermediate Similarity	NPD8034	Phase 2
0.7526	Intermediate Similarity	NPD8035	Phase 2
0.7447	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8133	Approved
0.708	Intermediate Similarity	NPD7327	Approved
0.708	Intermediate Similarity	NPD7328	Approved
0.7043	Intermediate Similarity	NPD8033	Approved
0.703	Intermediate Similarity	NPD7748	Approved
0.7019	Intermediate Similarity	NPD7640	Approved
0.7019	Intermediate Similarity	NPD7639	Approved
0.7018	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD7515	Phase 2
0.699	Remote Similarity	NPD7902	Approved
0.6989	Remote Similarity	NPD7645	Phase 2
0.6957	Remote Similarity	NPD8294	Approved
0.6957	Remote Similarity	NPD8377	Approved
0.6931	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD7638	Approved
0.6915	Remote Similarity	NPD7525	Registered
0.6897	Remote Similarity	NPD8379	Approved
0.6897	Remote Similarity	NPD8296	Approved
0.6897	Remote Similarity	NPD8335	Approved
0.6897	Remote Similarity	NPD8380	Approved
0.6897	Remote Similarity	NPD8378	Approved
0.6881	Remote Similarity	NPD6686	Approved
0.6804	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7503	Approved
0.6699	Remote Similarity	NPD7900	Approved
0.6699	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6604	Remote Similarity	NPD4225	Approved
0.6596	Remote Similarity	NPD6116	Phase 1
0.6574	Remote Similarity	NPD7632	Discontinued
0.6562	Remote Similarity	NPD6928	Phase 2
0.6559	Remote Similarity	NPD6942	Approved
0.6559	Remote Similarity	NPD7339	Approved
0.6504	Remote Similarity	NPD7319	Approved
0.65	Remote Similarity	NPD8328	Phase 3
0.6491	Remote Similarity	NPD6882	Approved
0.6489	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6117	Approved
0.6465	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4786	Approved
0.6452	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3667	Approved
0.6396	Remote Similarity	NPD6402	Approved
0.6396	Remote Similarity	NPD5739	Approved
0.6396	Remote Similarity	NPD6675	Approved
0.6396	Remote Similarity	NPD7128	Approved
0.6373	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6695	Phase 3
0.6364	Remote Similarity	NPD4788	Approved
0.6354	Remote Similarity	NPD6114	Approved
0.6354	Remote Similarity	NPD6697	Approved
0.6354	Remote Similarity	NPD6115	Approved
0.6354	Remote Similarity	NPD6118	Approved
0.6346	Remote Similarity	NPD7637	Suspended
0.6311	Remote Similarity	NPD6051	Approved
0.629	Remote Similarity	NPD7736	Approved
0.6286	Remote Similarity	NPD8171	Discontinued
0.6283	Remote Similarity	NPD6881	Approved
0.6283	Remote Similarity	NPD7320	Approved
0.6283	Remote Similarity	NPD6899	Approved
0.6271	Remote Similarity	NPD7115	Discovery
0.6228	Remote Similarity	NPD6372	Approved
0.6228	Remote Similarity	NPD6373	Approved
0.6204	Remote Similarity	NPD6083	Phase 2
0.6204	Remote Similarity	NPD6084	Phase 2
0.6195	Remote Similarity	NPD5697	Approved
0.6195	Remote Similarity	NPD5701	Approved
0.619	Remote Similarity	NPD6411	Approved
0.6176	Remote Similarity	NPD7146	Approved
0.6176	Remote Similarity	NPD7521	Approved
0.6176	Remote Similarity	NPD3618	Phase 1
0.6176	Remote Similarity	NPD5330	Approved
0.6176	Remote Similarity	NPD7334	Approved
0.6176	Remote Similarity	NPD6409	Approved
0.6176	Remote Similarity	NPD6684	Approved
0.6174	Remote Similarity	NPD7290	Approved
0.6174	Remote Similarity	NPD7102	Approved
0.6174	Remote Similarity	NPD6883	Approved
0.6154	Remote Similarity	NPD5328	Approved
0.6154	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6011	Approved
0.6122	Remote Similarity	NPD6929	Approved
0.6121	Remote Similarity	NPD6847	Approved
0.6121	Remote Similarity	NPD6617	Approved
0.6121	Remote Similarity	NPD6649	Approved
0.6121	Remote Similarity	NPD8130	Phase 1
0.6121	Remote Similarity	NPD6869	Approved
0.6121	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6650	Approved
0.6117	Remote Similarity	NPD7524	Approved
0.6117	Remote Similarity	NPD7750	Discontinued
0.6117	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6926	Approved
0.6105	Remote Similarity	NPD6924	Approved
0.61	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6012	Approved
0.6087	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6013	Approved
0.6087	Remote Similarity	NPD6014	Approved
0.608	Remote Similarity	NPD8293	Discontinued
0.6068	Remote Similarity	NPD8297	Approved
0.6064	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6930	Phase 2
0.6061	Remote Similarity	NPD7509	Discontinued
0.6061	Remote Similarity	NPD6931	Approved
0.6058	Remote Similarity	NPD6672	Approved
0.6058	Remote Similarity	NPD6903	Approved
0.6058	Remote Similarity	NPD5737	Approved
0.6042	Remote Similarity	NPD8264	Approved
0.604	Remote Similarity	NPD7154	Phase 3
0.6038	Remote Similarity	NPD6079	Approved
0.6022	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6370	Approved
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5982	Remote Similarity	NPD5211	Phase 2
0.5981	Remote Similarity	NPD5779	Approved
0.5981	Remote Similarity	NPD4202	Approved
0.5981	Remote Similarity	NPD5778	Approved
0.598	Remote Similarity	NPD3665	Phase 1
0.598	Remote Similarity	NPD3668	Phase 3
0.598	Remote Similarity	NPD3666	Approved
0.598	Remote Similarity	NPD3133	Approved
0.5979	Remote Similarity	NPD6933	Approved
0.5968	Remote Similarity	NPD6067	Discontinued
0.5935	Remote Similarity	NPD8513	Phase 3
0.5935	Remote Similarity	NPD8516	Approved
0.5935	Remote Similarity	NPD8515	Approved
0.5935	Remote Similarity	NPD8517	Approved
0.592	Remote Similarity	NPD7492	Approved
0.5918	Remote Similarity	NPD6925	Approved
0.5918	Remote Similarity	NPD5776	Phase 2
0.5909	Remote Similarity	NPD4755	Approved
0.59	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4748	Discontinued
0.5897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7151	Approved
0.5895	Remote Similarity	NPD5777	Approved
0.5895	Remote Similarity	NPD7152	Approved
0.5895	Remote Similarity	NPD7150	Approved
0.5893	Remote Similarity	NPD5344	Discontinued
0.5888	Remote Similarity	NPD7087	Discontinued
0.5882	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3669	Approved
0.5877	Remote Similarity	NPD5141	Approved
0.5873	Remote Similarity	NPD6616	Approved
0.5872	Remote Similarity	NPD5695	Phase 3
0.5859	Remote Similarity	NPD7145	Approved
0.5859	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5696	Approved
0.5854	Remote Similarity	NPD6054	Approved
0.5854	Remote Similarity	NPD6059	Approved
0.5851	Remote Similarity	NPD6923	Approved
0.5851	Remote Similarity	NPD6922	Approved
0.5843	Remote Similarity	NPD1145	Discontinued
0.5827	Remote Similarity	NPD7078	Approved
0.5826	Remote Similarity	NPD6008	Approved
0.582	Remote Similarity	NPD6335	Approved
0.5818	Remote Similarity	NPD4697	Phase 3
0.5818	Remote Similarity	NPD5221	Approved
0.5818	Remote Similarity	NPD5222	Approved
0.5818	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4250	Approved
0.581	Remote Similarity	NPD3573	Approved
0.581	Remote Similarity	NPD4251	Approved
0.5804	Remote Similarity	NPD5285	Approved
0.5804	Remote Similarity	NPD4700	Approved
0.5804	Remote Similarity	NPD5286	Approved
0.5804	Remote Similarity	NPD4696	Approved
0.5798	Remote Similarity	NPD6053	Discontinued
0.5789	Remote Similarity	NPD4787	Phase 1
0.5789	Remote Similarity	NPD7143	Approved
0.5789	Remote Similarity	NPD4245	Approved
0.5789	Remote Similarity	NPD4244	Approved
0.5789	Remote Similarity	NPD7144	Approved
0.5785	Remote Similarity	NPD6274	Approved
0.5785	Remote Similarity	NPD6940	Discontinued
0.5785	Remote Similarity	NPD6868	Approved
0.5773	Remote Similarity	NPD4785	Approved
0.5773	Remote Similarity	NPD1810	Approved
0.5773	Remote Similarity	NPD4784	Approved
0.5773	Remote Similarity	NPD1811	Approved
0.5772	Remote Similarity	NPD7101	Approved
0.5772	Remote Similarity	NPD7100	Approved
0.5769	Remote Similarity	NPD6893	Approved
0.5766	Remote Similarity	NPD5173	Approved
0.5755	Remote Similarity	NPD7625	Phase 1
0.5752	Remote Similarity	NPD5223	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