NPASS Compound

Structure

NPC232044 OpenBabel07101718312D 32 37 0 0 1 0 0 0 0 0999 V2000 -2.4271 -2.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8966 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7226 -1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7045 -2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -2.1756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3559 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2219 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0880 2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2219 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8200 2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8200 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0880 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2219 3.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -1.9945 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 2 15 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 25 1 0 0 0 0 9 20 1 0 0 0 0 10 19 1 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 31 1 0 0 0 0 14 1 1 6 0 0 0 15 24 1 0 0 0 0 15 27 1 6 0 0 0 16 9 1 6 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 26 1 1 0 0 0 18 25 1 1 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 28 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 30 1 1 0 0 0 23 11 1 1 0 0 0 23 24 1 0 0 0 0 23 32 1 0 0 0 0 24 25 1 1 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 27 8 1 1 0 0 0 27 31 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.32
Volume:	468.16
LogP:	4.084
LogD:	4.02
LogS:	-4.311
# Rotatable Bonds:	0
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	5.564
Fsp3:	1.0
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:	-4.818
MDCK Permeability:	2.3722877813270316e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.131
30% Bioavailability (F30%):	0.719

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	73.07710266113281%
Volume Distribution (VD):	1.278
Pgp-substrate:	7.892529010772705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.701
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	10.104
Half-life (T1/2):	0.385

ADMET: Toxicity

hERG Blockers:	0.987
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.96
Carcinogencity:	0.374
Eye Corrosion:	0.507
Eye Irritation:	0.299
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC232044

Natural Product ID:	NPC232044
*Common Name:**	Porrigenin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FYRLHXNMINIDCB-FJQPKSSRSA-N
Standard InCHI:	InChI=1S/C27H44O5/c1-14-5-8-27(31-13-14)15(2)24-23(32-27)11-18-16-9-20(28)19-10-21(29)22(30)12-26(19,4)17(16)6-7-25(18,24)3/h14-24,28-30H,5-13H2,1-4H3/t14-,15+,16-,17+,18+,19-,20-,21-,22+,23+,24+,25+,26-,27-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1C[C@@H](O)[C@@H]3[C@]([C@H]1CC2)(C)C[C@@H]([C@@H](C3)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512238
PubChem CID:	44566819
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33365	allium porrum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358643]

☑ 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	11

Activity Type	# Activity
Cell Line	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2486	Cell Line	IGR-1	Homo sapiens	IC50	=	942.0	ug.mL-1	PMID[516725]
NPT2486	Cell Line	IGR-1	Homo sapiens	IC50	=	471.0	ug.mL-1	PMID[516725]
NPT2486	Cell Line	IGR-1	Homo sapiens	IC50	=	184.0	ug.mL-1	PMID[516725]
NPT1886	Cell Line	J774	Mus musculus	IC50	=	754.0	ug.mL-1	PMID[516725]
NPT1886	Cell Line	J774	Mus musculus	IC50	=	515.0	ug.mL-1	PMID[516725]
NPT1886	Cell Line	J774	Mus musculus	IC50	=	270.0	ug.mL-1	PMID[516725]
NPT3470	Cell Line	WEHI-164	Mus musculus	IC50	=	277.0	ug.mL-1	PMID[516725]
NPT3470	Cell Line	WEHI-164	Mus musculus	IC50	=	110.0	ug.mL-1	PMID[516725]
NPT168	Cell Line	P388	Mus musculus	IC50	=	617.0	ug.mL-1	PMID[516725]
NPT168	Cell Line	P388	Mus musculus	IC50	=	270.0	ug.mL-1	PMID[516725]
NPT168	Cell Line	P388	Mus musculus	IC50	=	115.0	ug.mL-1	PMID[516725]

☑ 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 NPC232044 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	485
0.1-0.2	4600
0.2-0.3	13938
0.3-0.4	10810
0.4-0.5	5161
0.5-0.6	4170
0.6-0.7	2386
0.7-0.8	874
0.8-0.85	121
0.85-0.9	133
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC273290
0.9873	High Similarity	NPC227260
0.962	High Similarity	NPC296734
0.9375	High Similarity	NPC470611
0.9367	High Similarity	NPC7479
0.9367	High Similarity	NPC248944
0.9367	High Similarity	NPC257296
0.9294	High Similarity	NPC5632
0.9294	High Similarity	NPC149966
0.9176	High Similarity	NPC473542
0.9167	High Similarity	NPC128475
0.9157	High Similarity	NPC471240
0.908	High Similarity	NPC3538
0.908	High Similarity	NPC113500
0.908	High Similarity	NPC477224
0.9059	High Similarity	NPC20822
0.9059	High Similarity	NPC228059
0.9059	High Similarity	NPC473472
0.9048	High Similarity	NPC210658
0.9048	High Similarity	NPC161928
0.8966	High Similarity	NPC167644
0.8966	High Similarity	NPC144790
0.8966	High Similarity	NPC311246
0.8966	High Similarity	NPC88962
0.8966	High Similarity	NPC149400
0.8953	High Similarity	NPC223143
0.8941	High Similarity	NPC281004
0.8876	High Similarity	NPC121453
0.8864	High Similarity	NPC253268
0.8864	High Similarity	NPC24960
0.8864	High Similarity	NPC252253
0.8864	High Similarity	NPC30687
0.8864	High Similarity	NPC222731
0.8864	High Similarity	NPC312678
0.8864	High Similarity	NPC179859
0.8864	High Similarity	NPC473774
0.8864	High Similarity	NPC475436
0.8864	High Similarity	NPC291547
0.8864	High Similarity	NPC473851
0.8864	High Similarity	NPC294686
0.8864	High Similarity	NPC131693
0.8864	High Similarity	NPC174024
0.8864	High Similarity	NPC45959
0.8864	High Similarity	NPC175
0.8851	High Similarity	NPC59006
0.8851	High Similarity	NPC293609
0.8837	High Similarity	NPC102725
0.8837	High Similarity	NPC82955
0.881	High Similarity	NPC290612
0.8795	High Similarity	NPC470070
0.8778	High Similarity	NPC477222
0.8778	High Similarity	NPC477223
0.8764	High Similarity	NPC473065
0.8764	High Similarity	NPC473067
0.8764	High Similarity	NPC473064
0.875	High Similarity	NPC182740
0.875	High Similarity	NPC234352
0.875	High Similarity	NPC177834
0.875	High Similarity	NPC256104
0.875	High Similarity	NPC141769
0.875	High Similarity	NPC250393
0.875	High Similarity	NPC122083
0.875	High Similarity	NPC477451
0.875	High Similarity	NPC476669
0.875	High Similarity	NPC211845
0.875	High Similarity	NPC277774
0.875	High Similarity	NPC48339
0.875	High Similarity	NPC297348
0.875	High Similarity	NPC249204
0.875	High Similarity	NPC325828
0.875	High Similarity	NPC477547
0.8736	High Similarity	NPC279329
0.8736	High Similarity	NPC65550
0.8681	High Similarity	NPC473518
0.8681	High Similarity	NPC473638
0.8667	High Similarity	NPC304011
0.8667	High Similarity	NPC473601
0.8667	High Similarity	NPC142264
0.8667	High Similarity	NPC476510
0.8667	High Similarity	NPC156377
0.8667	High Similarity	NPC139271
0.8667	High Similarity	NPC195297
0.8652	High Similarity	NPC475325
0.8652	High Similarity	NPC217205
0.8652	High Similarity	NPC291203
0.8652	High Similarity	NPC264101
0.8652	High Similarity	NPC471464
0.8636	High Similarity	NPC473830
0.8636	High Similarity	NPC36372
0.8636	High Similarity	NPC229801
0.8636	High Similarity	NPC476668
0.8636	High Similarity	NPC473637
0.8636	High Similarity	NPC210759
0.8636	High Similarity	NPC307167
0.8636	High Similarity	NPC204881
0.8605	High Similarity	NPC43912
0.8605	High Similarity	NPC140446
0.8571	High Similarity	NPC232611
0.8571	High Similarity	NPC233649
0.8571	High Similarity	NPC115165
0.8571	High Similarity	NPC307534
0.8571	High Similarity	NPC470861
0.8571	High Similarity	NPC470862
0.8571	High Similarity	NPC303069
0.8571	High Similarity	NPC470028
0.8571	High Similarity	NPC475207
0.8571	High Similarity	NPC83137
0.8571	High Similarity	NPC476112
0.8571	High Similarity	NPC51520
0.8556	High Similarity	NPC211354
0.8556	High Similarity	NPC474399
0.8556	High Similarity	NPC473727
0.8556	High Similarity	NPC6295
0.8556	High Similarity	NPC475351
0.8556	High Similarity	NPC92196
0.8556	High Similarity	NPC107962
0.8556	High Similarity	NPC107188
0.8556	High Similarity	NPC473610
0.8556	High Similarity	NPC206003
0.8556	High Similarity	NPC19400
0.8539	High Similarity	NPC172838
0.8539	High Similarity	NPC137004
0.8539	High Similarity	NPC473726
0.8519	High Similarity	NPC64081
0.8519	High Similarity	NPC474574
0.8495	Intermediate Similarity	NPC477225
0.8481	Intermediate Similarity	NPC470610
0.8478	Intermediate Similarity	NPC473616
0.8478	Intermediate Similarity	NPC291548
0.8462	Intermediate Similarity	NPC116756
0.8462	Intermediate Similarity	NPC103616
0.8462	Intermediate Similarity	NPC160426
0.8462	Intermediate Similarity	NPC98018
0.8462	Intermediate Similarity	NPC470866
0.8462	Intermediate Similarity	NPC132080
0.8462	Intermediate Similarity	NPC470863
0.8462	Intermediate Similarity	NPC287483
0.8462	Intermediate Similarity	NPC475643
0.8462	Intermediate Similarity	NPC475625
0.8462	Intermediate Similarity	NPC473287
0.8462	Intermediate Similarity	NPC470864
0.8462	Intermediate Similarity	NPC184617
0.8462	Intermediate Similarity	NPC284104
0.8462	Intermediate Similarity	NPC232037
0.8462	Intermediate Similarity	NPC470865
0.8462	Intermediate Similarity	NPC128572
0.8462	Intermediate Similarity	NPC84111
0.8462	Intermediate Similarity	NPC30856
0.8462	Intermediate Similarity	NPC97700
0.8452	Intermediate Similarity	NPC475388
0.8444	Intermediate Similarity	NPC305418
0.8444	Intermediate Similarity	NPC309866
0.8444	Intermediate Similarity	NPC473503
0.8409	Intermediate Similarity	NPC131466
0.8404	Intermediate Similarity	NPC228049
0.8404	Intermediate Similarity	NPC52585
0.8404	Intermediate Similarity	NPC68630
0.8395	Intermediate Similarity	NPC163597
0.8391	Intermediate Similarity	NPC472396
0.8387	Intermediate Similarity	NPC470030
0.8375	Intermediate Similarity	NPC48795
0.8372	Intermediate Similarity	NPC266651
0.837	Intermediate Similarity	NPC274200
0.8352	Intermediate Similarity	NPC469710
0.8352	Intermediate Similarity	NPC305808
0.8333	Intermediate Similarity	NPC161035
0.8313	Intermediate Similarity	NPC477282
0.8313	Intermediate Similarity	NPC81074
0.8298	Intermediate Similarity	NPC108227
0.8298	Intermediate Similarity	NPC472081
0.8298	Intermediate Similarity	NPC476512
0.8298	Intermediate Similarity	NPC475574
0.8293	Intermediate Similarity	NPC128951
0.8293	Intermediate Similarity	NPC133596
0.8293	Intermediate Similarity	NPC105208
0.8293	Intermediate Similarity	NPC302578
0.8293	Intermediate Similarity	NPC477227
0.8293	Intermediate Similarity	NPC11907
0.8293	Intermediate Similarity	NPC192046
0.8272	Intermediate Similarity	NPC270306
0.8272	Intermediate Similarity	NPC91387
0.8272	Intermediate Similarity	NPC317242
0.8272	Intermediate Similarity	NPC231680
0.8261	Intermediate Similarity	NPC296936
0.8261	Intermediate Similarity	NPC237071
0.8261	Intermediate Similarity	NPC238796
0.8261	Intermediate Similarity	NPC203434
0.8256	Intermediate Similarity	NPC320824
0.8256	Intermediate Similarity	NPC474156
0.825	Intermediate Similarity	NPC153719
0.8228	Intermediate Similarity	NPC63588
0.8228	Intermediate Similarity	NPC232925
0.8228	Intermediate Similarity	NPC251201
0.8211	Intermediate Similarity	NPC134967
0.8211	Intermediate Similarity	NPC310138
0.8211	Intermediate Similarity	NPC114700
0.8211	Intermediate Similarity	NPC470029
0.8193	Intermediate Similarity	NPC67657
0.8193	Intermediate Similarity	NPC18857
0.8172	Intermediate Similarity	NPC470591

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 NPC232044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	472
0.1-0.2	4398
0.2-0.3	3048
0.3-0.4	660
0.4-0.5	286
0.5-0.6	208
0.6-0.7	71
0.7-0.8	4
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9367	High Similarity	NPD6928	Phase 2
0.875	High Similarity	NPD8171	Discontinued
0.7957	Intermediate Similarity	NPD7991	Discontinued
0.7857	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6115	Approved
0.7159	Intermediate Similarity	NPD6118	Approved
0.7159	Intermediate Similarity	NPD6114	Approved
0.7159	Intermediate Similarity	NPD6697	Approved
0.7143	Intermediate Similarity	NPD4787	Phase 1
0.7091	Intermediate Similarity	NPD7516	Approved
0.7045	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.6932	Remote Similarity	NPD6117	Approved
0.6897	Remote Similarity	NPD1810	Approved
0.6897	Remote Similarity	NPD1811	Approved
0.6875	Remote Similarity	NPD8377	Approved
0.6875	Remote Similarity	NPD8294	Approved
0.6814	Remote Similarity	NPD8380	Approved
0.6814	Remote Similarity	NPD8379	Approved
0.6814	Remote Similarity	NPD8296	Approved
0.6814	Remote Similarity	NPD8335	Approved
0.6814	Remote Similarity	NPD8378	Approved
0.6814	Remote Similarity	NPD8033	Approved
0.6744	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD8133	Approved
0.663	Remote Similarity	NPD7525	Registered
0.6629	Remote Similarity	NPD3703	Phase 2
0.6627	Remote Similarity	NPD371	Approved
0.6581	Remote Similarity	NPD7507	Approved
0.6552	Remote Similarity	NPD4245	Approved
0.6552	Remote Similarity	NPD4244	Approved
0.6552	Remote Similarity	NPD2686	Approved
0.6552	Remote Similarity	NPD2254	Approved
0.6552	Remote Similarity	NPD2687	Approved
0.6518	Remote Similarity	NPD6940	Discontinued
0.6481	Remote Similarity	NPD8174	Phase 2
0.6444	Remote Similarity	NPD3702	Approved
0.6437	Remote Similarity	NPD3698	Phase 2
0.6437	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6059	Approved
0.6435	Remote Similarity	NPD6054	Approved
0.6422	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7319	Approved
0.64	Remote Similarity	NPD8034	Phase 2
0.64	Remote Similarity	NPD8035	Phase 2
0.6379	Remote Similarity	NPD7503	Approved
0.6346	Remote Similarity	NPD7638	Approved
0.6333	Remote Similarity	NPD7736	Approved
0.6325	Remote Similarity	NPD6370	Approved
0.6292	Remote Similarity	NPD5777	Approved
0.6289	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7639	Approved
0.6286	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3669	Approved
0.6239	Remote Similarity	NPD6016	Approved
0.6239	Remote Similarity	NPD6015	Approved
0.6226	Remote Similarity	NPD1700	Approved
0.6218	Remote Similarity	NPD7492	Approved
0.6186	Remote Similarity	NPD5988	Approved
0.618	Remote Similarity	NPD4789	Approved
0.6168	Remote Similarity	NPD7632	Discontinued
0.6167	Remote Similarity	NPD6616	Approved
0.6139	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6700	Approved
0.6136	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5360	Phase 3
0.6134	Remote Similarity	NPD6067	Discontinued
0.6116	Remote Similarity	NPD8293	Discontinued
0.6116	Remote Similarity	NPD7078	Approved
0.6078	Remote Similarity	NPD6702	Approved
0.6078	Remote Similarity	NPD6703	Approved
0.6066	Remote Similarity	NPD6033	Approved
0.6061	Remote Similarity	NPD8308	Discontinued
0.6034	Remote Similarity	NPD6009	Approved
0.6034	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD8449	Approved
0.6	Remote Similarity	NPD7645	Phase 2
0.5977	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6882	Approved
0.5952	Remote Similarity	NPD8450	Suspended
0.5938	Remote Similarity	NPD4748	Discontinued
0.5934	Remote Similarity	NPD6081	Approved
0.5914	Remote Similarity	NPD7339	Approved
0.5914	Remote Similarity	NPD6942	Approved
0.5913	Remote Similarity	NPD4632	Approved
0.5895	Remote Similarity	NPD3671	Phase 1
0.5893	Remote Similarity	NPD7320	Approved
0.5893	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5739	Approved
0.5856	Remote Similarity	NPD6402	Approved
0.5856	Remote Similarity	NPD6008	Approved
0.5856	Remote Similarity	NPD7128	Approved
0.5856	Remote Similarity	NPD6675	Approved
0.5842	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8418	Phase 2
0.5804	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4159	Approved
0.5778	Remote Similarity	NPD7625	Phase 1
0.5778	Remote Similarity	NPD6705	Phase 1
0.5761	Remote Similarity	NPD4758	Discontinued
0.5758	Remote Similarity	NPD4788	Approved
0.5758	Remote Similarity	NPD6695	Phase 3
0.5752	Remote Similarity	NPD6899	Approved
0.5752	Remote Similarity	NPD6686	Approved
0.5752	Remote Similarity	NPD6881	Approved
0.575	Remote Similarity	NPD6319	Approved
0.5738	Remote Similarity	NPD8328	Phase 3
0.573	Remote Similarity	NPD4224	Phase 2
0.5729	Remote Similarity	NPD4238	Approved
0.5729	Remote Similarity	NPD4802	Phase 2
0.5729	Remote Similarity	NPD5364	Discontinued
0.5714	Remote Similarity	NPD1780	Approved
0.5714	Remote Similarity	NPD4202	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD1779	Approved
0.5702	Remote Similarity	NPD6372	Approved
0.5702	Remote Similarity	NPD6373	Approved
0.5702	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.569	Remote Similarity	NPD8297	Approved
0.5684	Remote Similarity	NPD6933	Approved
0.5678	Remote Similarity	NPD7754	Approved
0.5678	Remote Similarity	NPD7755	Approved
0.5664	Remote Similarity	NPD5697	Approved
0.5664	Remote Similarity	NPD5701	Approved
0.5652	Remote Similarity	NPD6883	Approved
0.5652	Remote Similarity	NPD7290	Approved
0.5652	Remote Similarity	NPD7102	Approved
0.5652	Remote Similarity	NPD4634	Approved
0.5648	Remote Similarity	NPD4755	Approved
0.5625	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6011	Approved
0.561	Remote Similarity	NPD7604	Phase 2
0.5603	Remote Similarity	NPD6649	Approved
0.5603	Remote Similarity	NPD6650	Approved
0.5603	Remote Similarity	NPD6617	Approved
0.5603	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD6869	Approved
0.5603	Remote Similarity	NPD6847	Approved
0.5603	Remote Similarity	NPD8130	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