NPASS Compound

Structure

NPC143092 OpenBabel07101719252D 32 35 0 0 1 0 0 0 0 0999 V2000 3.9417 5.7469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6129 2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5583 4.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1488 -0.5583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 6.6129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7469 -0.0583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7346 2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4417 0.7346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9417 4.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0148 2.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1564 0.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7346 1.4417 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4417 0.7346 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4417 3.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1488 2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 3.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1488 1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4417 4.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8808 2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9417 4.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0148 0.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 4.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8808 1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9877 -0.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 -1.0474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9417 5.7469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7469 2.9417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0583 4.0148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0148 -0.0583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9417 5.7469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7469 0.9417 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 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 32 1 0 0 0 0 12 7 1 6 0 0 0 12 13 1 0 0 0 0 13 8 1 1 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 20 2 0 0 0 0 17 21 2 0 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 28 1 0 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 25 2 0 0 0 0 24 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.18
Volume:	441.301
LogP:	3.116
LogD:	2.904
LogS:	-4.177
# Rotatable Bonds:	6
TPSA:	81.68
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	3.576
Fsp3:	0.458
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:	-4.684
MDCK Permeability:	2.886338006646838e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	76.2257080078125%
Volume Distribution (VD):	0.603
Pgp-substrate:	21.523090362548828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.986
CYP2C19-inhibitor:	0.462
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.189
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.729
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	6.793
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.349
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.715
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.284
Maximum Recommended Daily Dose:	0.229
Skin Sensitization:	0.706
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.476

Download Data

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

Natural Product: NPC143092

Natural Product ID:	NPC143092
*Common Name:**	Steganolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZSPMNJCSHBZQPT-QWHCGFSZSA-N
Standard InCHI:	InChI=1S/C24H28O8/c1-26-18-9-14-15-10-19(27-2)23(31-6)21(29-4)17(15)8-13-12(11-32-24(13)25)7-16(14)20(28-3)22(18)30-5/h9-10,12-13H,7-8,11H2,1-6H3/t12-,13+/m0/s1
SMILES:	COc1cc2-c3cc(c(c(c3C[C@@H]3[C@@H](Cc2c(c1OC)OC)COC3=O)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470472
PubChem CID:	10072143
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

*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
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720541]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6208342]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[8133298]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
ED50	11
Others	6

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	9.0	ug ml-1	PMID[543718]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	5.5	ug ml-1	PMID[543718]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	9.2	ug ml-1	PMID[543718]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	8.9	ug ml-1	PMID[543718]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	5.5	ug ml-1	PMID[543718]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	5.1	ug ml-1	PMID[543718]
NPT2049	Cell Line	HT	Homo sapiens	ED50	=	6.5	ug ml-1	PMID[543718]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.9	ug ml-1	PMID[543718]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.1	ug ml-1	PMID[543718]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[543718]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[543718]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.0	ug ml-1	PMID[543718]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.8	ug ml-1	PMID[543718]

☑ 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 NPC143092 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	374
0.1-0.2	1520
0.2-0.3	3416
0.3-0.4	8771
0.4-0.5	10284
0.5-0.6	3811
0.6-0.7	8389
0.7-0.8	5730
0.8-0.85	312
0.85-0.9	80
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9854	High Similarity	NPC18211
0.927	High Similarity	NPC72796
0.927	High Similarity	NPC44245
0.9241	High Similarity	NPC303519
0.913	High Similarity	NPC211386
0.9116	High Similarity	NPC474514
0.9067	High Similarity	NPC325122
0.906	High Similarity	NPC477380
0.9054	High Similarity	NPC178195
0.9054	High Similarity	NPC348849
0.9028	High Similarity	NPC321958
0.9028	High Similarity	NPC321696
0.9	High Similarity	NPC865
0.9	High Similarity	NPC477885
0.8958	High Similarity	NPC318286
0.8958	High Similarity	NPC327651
0.8951	High Similarity	NPC218510
0.8951	High Similarity	NPC76415
0.8929	High Similarity	NPC471182
0.8926	High Similarity	NPC273578
0.8912	High Similarity	NPC149505
0.8889	High Similarity	NPC61141
0.8889	High Similarity	NPC326144
0.8881	High Similarity	NPC40237
0.8881	High Similarity	NPC151423
0.8819	High Similarity	NPC470811
0.8819	High Similarity	NPC477697
0.8819	High Similarity	NPC477696
0.8792	High Similarity	NPC104353
0.8792	High Similarity	NPC220577
0.8784	High Similarity	NPC316989
0.8776	High Similarity	NPC252281
0.8776	High Similarity	NPC198129
0.8776	High Similarity	NPC477375
0.8776	High Similarity	NPC327352
0.8767	High Similarity	NPC87295
0.8759	High Similarity	NPC92693
0.8759	High Similarity	NPC218841
0.8759	High Similarity	NPC475000
0.8759	High Similarity	NPC474036
0.875	High Similarity	NPC210354
0.875	High Similarity	NPC176586
0.8742	High Similarity	NPC238834
0.8725	High Similarity	NPC210642
0.8725	High Similarity	NPC13985
0.8716	High Similarity	NPC477376
0.8716	High Similarity	NPC477374
0.8716	High Similarity	NPC322426
0.8716	High Similarity	NPC85141
0.8707	High Similarity	NPC101755
0.8707	High Similarity	NPC80230
0.8707	High Similarity	NPC104024
0.8707	High Similarity	NPC65574
0.8707	High Similarity	NPC304687
0.869	High Similarity	NPC273657
0.869	High Similarity	NPC106920
0.8654	High Similarity	NPC477884
0.8649	High Similarity	NPC325720
0.8649	High Similarity	NPC304821
0.8649	High Similarity	NPC316676
0.8649	High Similarity	NPC477879
0.8639	High Similarity	NPC193779
0.863	High Similarity	NPC191158
0.863	High Similarity	NPC177644
0.863	High Similarity	NPC87883
0.8609	High Similarity	NPC178574
0.8609	High Similarity	NPC65591
0.8609	High Similarity	NPC474606
0.8609	High Similarity	NPC475116
0.86	High Similarity	NPC475756
0.8591	High Similarity	NPC177476
0.8591	High Similarity	NPC262455
0.8581	High Similarity	NPC295297
0.8581	High Similarity	NPC319749
0.8581	High Similarity	NPC191352
0.8581	High Similarity	NPC258322
0.8571	High Similarity	NPC141493
0.8571	High Similarity	NPC27106
0.8571	High Similarity	NPC184928
0.8562	High Similarity	NPC474288
0.8562	High Similarity	NPC29727
0.8553	High Similarity	NPC473425
0.8551	High Similarity	NPC223807
0.8544	High Similarity	NPC471180
0.8543	High Similarity	NPC471154
0.8543	High Similarity	NPC473732
0.8533	High Similarity	NPC473989
0.8531	High Similarity	NPC209229
0.8526	High Similarity	NPC280778
0.8523	High Similarity	NPC262804
0.8523	High Similarity	NPC40654
0.8521	High Similarity	NPC145722
0.8521	High Similarity	NPC256776
0.8521	High Similarity	NPC185680
0.8516	High Similarity	NPC474770
0.8514	High Similarity	NPC213482
0.8514	High Similarity	NPC474054
0.8511	High Similarity	NPC475856
0.8506	High Similarity	NPC19947
0.8506	High Similarity	NPC207584
0.8506	High Similarity	NPC181168
0.8506	High Similarity	NPC163527
0.8506	High Similarity	NPC115281
0.85	High Similarity	NPC178737
0.8489	Intermediate Similarity	NPC207702
0.8489	Intermediate Similarity	NPC283114
0.8489	Intermediate Similarity	NPC149008
0.8487	Intermediate Similarity	NPC217708
0.8487	Intermediate Similarity	NPC77237
0.8487	Intermediate Similarity	NPC308739
0.8487	Intermediate Similarity	NPC245948
0.8487	Intermediate Similarity	NPC53669
0.8487	Intermediate Similarity	NPC477377
0.8487	Intermediate Similarity	NPC126405
0.8487	Intermediate Similarity	NPC24562
0.8487	Intermediate Similarity	NPC297271
0.8487	Intermediate Similarity	NPC16791
0.8477	Intermediate Similarity	NPC474975
0.8477	Intermediate Similarity	NPC224472
0.8471	Intermediate Similarity	NPC475865
0.8467	Intermediate Similarity	NPC474965
0.8467	Intermediate Similarity	NPC174512
0.8467	Intermediate Similarity	NPC474347
0.8467	Intermediate Similarity	NPC125570
0.8467	Intermediate Similarity	NPC474393
0.8467	Intermediate Similarity	NPC668
0.8467	Intermediate Similarity	NPC477695
0.8467	Intermediate Similarity	NPC293757
0.8467	Intermediate Similarity	NPC477698
0.8456	Intermediate Similarity	NPC183083
0.8456	Intermediate Similarity	NPC137352
0.8452	Intermediate Similarity	NPC474043
0.8446	Intermediate Similarity	NPC470932
0.8442	Intermediate Similarity	NPC32373
0.8442	Intermediate Similarity	NPC301897
0.8442	Intermediate Similarity	NPC237946
0.8438	Intermediate Similarity	NPC477883
0.8431	Intermediate Similarity	NPC198461
0.8431	Intermediate Similarity	NPC312763
0.8429	Intermediate Similarity	NPC153547
0.8421	Intermediate Similarity	NPC272566
0.8421	Intermediate Similarity	NPC475229
0.8421	Intermediate Similarity	NPC477378
0.8421	Intermediate Similarity	NPC228662
0.8414	Intermediate Similarity	NPC470962
0.8411	Intermediate Similarity	NPC477381
0.8411	Intermediate Similarity	NPC470916
0.8403	Intermediate Similarity	NPC143895
0.8403	Intermediate Similarity	NPC32189
0.8403	Intermediate Similarity	NPC11453
0.8397	Intermediate Similarity	NPC96593
0.8397	Intermediate Similarity	NPC63061
0.8389	Intermediate Similarity	NPC474446
0.8385	Intermediate Similarity	NPC471181
0.8377	Intermediate Similarity	NPC476065
0.8365	Intermediate Similarity	NPC83049
0.8365	Intermediate Similarity	NPC118162
0.8365	Intermediate Similarity	NPC320471
0.8355	Intermediate Similarity	NPC164082
0.8355	Intermediate Similarity	NPC477379
0.8355	Intermediate Similarity	NPC477700
0.8354	Intermediate Similarity	NPC469475
0.8354	Intermediate Similarity	NPC469518
0.8344	Intermediate Similarity	NPC288149
0.8344	Intermediate Similarity	NPC239890
0.8344	Intermediate Similarity	NPC209411
0.8344	Intermediate Similarity	NPC145569
0.8344	Intermediate Similarity	NPC216223
0.8333	Intermediate Similarity	NPC477881
0.8333	Intermediate Similarity	NPC328122
0.8333	Intermediate Similarity	NPC474568
0.8333	Intermediate Similarity	NPC125713
0.8323	Intermediate Similarity	NPC150227
0.8323	Intermediate Similarity	NPC474983
0.8323	Intermediate Similarity	NPC469474
0.8323	Intermediate Similarity	NPC473323
0.8322	Intermediate Similarity	NPC474158
0.8313	Intermediate Similarity	NPC42230
0.8313	Intermediate Similarity	NPC311912
0.8313	Intermediate Similarity	NPC79322
0.8312	Intermediate Similarity	NPC103197
0.8312	Intermediate Similarity	NPC30009
0.8311	Intermediate Similarity	NPC324962
0.8302	Intermediate Similarity	NPC474647
0.8302	Intermediate Similarity	NPC475953
0.8301	Intermediate Similarity	NPC476434
0.8301	Intermediate Similarity	NPC477699
0.8301	Intermediate Similarity	NPC56184
0.8291	Intermediate Similarity	NPC473445
0.8291	Intermediate Similarity	NPC469512
0.8291	Intermediate Similarity	NPC42797
0.8291	Intermediate Similarity	NPC249070
0.8288	Intermediate Similarity	NPC290714
0.8288	Intermediate Similarity	NPC53722
0.8288	Intermediate Similarity	NPC201404
0.828	Intermediate Similarity	NPC268718
0.828	Intermediate Similarity	NPC150943
0.828	Intermediate Similarity	NPC119910
0.828	Intermediate Similarity	NPC91634
0.828	Intermediate Similarity	NPC470637

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 NPC143092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	913
0.2-0.3	1787
0.3-0.4	2683
0.4-0.5	1850
0.5-0.6	1046
0.6-0.7	467
0.7-0.8	94
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8487	Intermediate Similarity	NPD37	Approved
0.8462	Intermediate Similarity	NPD7199	Phase 2
0.8442	Intermediate Similarity	NPD4967	Phase 2
0.8442	Intermediate Similarity	NPD4965	Approved
0.8442	Intermediate Similarity	NPD4966	Approved
0.8354	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6234	Discontinued
0.8158	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.7986	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7228	Approved
0.7962	Intermediate Similarity	NPD1465	Phase 2
0.7937	Intermediate Similarity	NPD5494	Approved
0.7911	Intermediate Similarity	NPD3817	Phase 2
0.7862	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7229	Phase 3
0.7818	Intermediate Similarity	NPD5844	Phase 1
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7784	Intermediate Similarity	NPD7240	Approved
0.7764	Intermediate Similarity	NPD919	Approved
0.775	Intermediate Similarity	NPD3882	Suspended
0.7748	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7819	Suspended
0.7733	Intermediate Similarity	NPD2438	Suspended
0.7727	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2533	Approved
0.7677	Intermediate Similarity	NPD2534	Approved
0.7677	Intermediate Similarity	NPD2532	Approved
0.7606	Intermediate Similarity	NPD3705	Approved
0.7589	Intermediate Similarity	NPD17	Approved
0.7576	Intermediate Similarity	NPD5242	Approved
0.7562	Intermediate Similarity	NPD1934	Approved
0.755	Intermediate Similarity	NPD3748	Approved
0.7545	Intermediate Similarity	NPD3818	Discontinued
0.7534	Intermediate Similarity	NPD3018	Phase 2
0.7517	Intermediate Similarity	NPD2979	Phase 3
0.7516	Intermediate Similarity	NPD2801	Approved
0.7516	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6799	Approved
0.7483	Intermediate Similarity	NPD1281	Approved
0.7469	Intermediate Similarity	NPD5353	Approved
0.7468	Intermediate Similarity	NPD920	Approved
0.7467	Intermediate Similarity	NPD6355	Discontinued
0.7464	Intermediate Similarity	NPD5283	Phase 1
0.7455	Intermediate Similarity	NPD1247	Approved
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6599	Discontinued
0.7432	Intermediate Similarity	NPD3027	Phase 3
0.7431	Intermediate Similarity	NPD1608	Approved
0.7431	Intermediate Similarity	NPD2981	Phase 2
0.7419	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4110	Phase 3
0.7407	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6099	Approved
0.7386	Intermediate Similarity	NPD6100	Approved
0.7386	Intermediate Similarity	NPD2796	Approved
0.7379	Intermediate Similarity	NPD2982	Phase 2
0.7379	Intermediate Similarity	NPD2983	Phase 2
0.7355	Intermediate Similarity	NPD1243	Approved
0.7351	Intermediate Similarity	NPD230	Phase 1
0.7346	Intermediate Similarity	NPD6801	Discontinued
0.7329	Intermediate Similarity	NPD1283	Approved
0.7321	Intermediate Similarity	NPD6166	Phase 2
0.7321	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3750	Approved
0.7301	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7284	Intermediate Similarity	NPD6386	Approved
0.7284	Intermediate Similarity	NPD6385	Approved
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD1651	Approved
0.7273	Intermediate Similarity	NPD2531	Phase 2
0.7251	Intermediate Similarity	NPD7074	Phase 3
0.7246	Intermediate Similarity	NPD6959	Discontinued
0.7233	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3787	Discontinued
0.7197	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4628	Phase 3
0.7193	Intermediate Similarity	NPD7054	Approved
0.7181	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7411	Suspended
0.7171	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1613	Approved
0.717	Intermediate Similarity	NPD1511	Approved
0.7162	Intermediate Similarity	NPD3266	Approved
0.7162	Intermediate Similarity	NPD3267	Approved
0.7153	Intermediate Similarity	NPD5691	Approved
0.7152	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7151	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5536	Phase 2
0.7133	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4908	Phase 1
0.7125	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3146	Approved
0.7117	Intermediate Similarity	NPD4380	Phase 2
0.7105	Intermediate Similarity	NPD8032	Phase 2
0.7101	Intermediate Similarity	NPD5710	Approved
0.7101	Intermediate Similarity	NPD5711	Approved
0.7097	Intermediate Similarity	NPD7033	Discontinued
0.7097	Intermediate Similarity	NPD1510	Phase 2
0.7081	Intermediate Similarity	NPD1512	Approved
0.7073	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1240	Approved
0.7051	Intermediate Similarity	NPD3539	Phase 1
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5402	Approved
0.7047	Intermediate Similarity	NPD2797	Approved
0.7044	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3268	Approved
0.7039	Intermediate Similarity	NPD1296	Phase 2
0.7039	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5585	Approved
0.7029	Intermediate Similarity	NPD7808	Phase 3
0.7025	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6832	Phase 2
0.7019	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1933	Approved
0.7011	Intermediate Similarity	NPD6797	Phase 2
0.7007	Intermediate Similarity	NPD1610	Phase 2
0.7006	Intermediate Similarity	NPD3540	Phase 1
0.7006	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD7768	Phase 2
0.7006	Intermediate Similarity	NPD5762	Approved
0.6989	Remote Similarity	NPD7680	Approved
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4625	Phase 3
0.6971	Remote Similarity	NPD7685	Pre-registration
0.6971	Remote Similarity	NPD6559	Discontinued
0.6971	Remote Similarity	NPD7251	Discontinued
0.6968	Remote Similarity	NPD1607	Approved
0.6966	Remote Similarity	NPD8434	Phase 2
0.6964	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1549	Phase 2
0.6962	Remote Similarity	NPD2897	Discontinued
0.6957	Remote Similarity	NPD4357	Discontinued
0.6951	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2935	Discontinued
0.6943	Remote Similarity	NPD4476	Approved
0.6943	Remote Similarity	NPD4477	Approved
0.6936	Remote Similarity	NPD3751	Discontinued
0.6935	Remote Similarity	NPD5005	Approved
0.6935	Remote Similarity	NPD5006	Approved
0.6933	Remote Similarity	NPD5403	Approved
0.6928	Remote Similarity	NPD3764	Approved
0.6919	Remote Similarity	NPD2403	Approved
0.6918	Remote Similarity	NPD2800	Approved
0.6914	Remote Similarity	NPD5401	Approved
0.6909	Remote Similarity	NPD6876	Approved
0.6909	Remote Similarity	NPD6875	Approved
0.6903	Remote Similarity	NPD447	Suspended
0.6899	Remote Similarity	NPD6004	Phase 3
0.6899	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6005	Phase 3
0.6899	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6002	Phase 3
0.6894	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7124	Phase 2
0.6892	Remote Similarity	NPD1611	Approved
0.689	Remote Similarity	NPD1653	Approved
0.6887	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8455	Phase 2
0.6883	Remote Similarity	NPD6233	Phase 2
0.6882	Remote Similarity	NPD6746	Phase 2
0.6879	Remote Similarity	NPD2799	Discontinued
0.6871	Remote Similarity	NPD1778	Approved
0.6871	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4626	Approved
0.6867	Remote Similarity	NPD1876	Approved
0.6864	Remote Similarity	NPD4055	Discovery
0.6863	Remote Similarity	NPD7095	Approved
0.6848	Remote Similarity	NPD4005	Discontinued
0.6848	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3226	Approved
0.6845	Remote Similarity	NPD5978	Approved
0.6845	Remote Similarity	NPD5977	Approved
0.6839	Remote Similarity	NPD943	Approved
0.6835	Remote Similarity	NPD1551	Phase 2
0.6829	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4481	Phase 3
0.6818	Remote Similarity	NPD5111	Phase 2
0.6818	Remote Similarity	NPD5110	Phase 2
0.6818	Remote Similarity	NPD5109	Approved
0.6815	Remote Similarity	NPD6111	Discontinued
0.6813	Remote Similarity	NPD2654	Approved
0.6813	Remote Similarity	NPD6674	Discontinued

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