NPASS Compound

Structure

CID142352 OpenBabel06191715502D 25 28 0 0 1 0 0 0 0 0999 V2000 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2086 -0.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9711 -0.0384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9879 -2.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5487 -1.3518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1431 -1.8437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 0.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4506 0.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4200 -0.3805 0.0000 C 0 0 2 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 0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2647 -0.5403 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8592 -1.0321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6927 1.0945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2990 1.8456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 18 1 0 0 0 0 9 21 2 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 7 1 1 0 0 0 11 15 1 0 0 0 0 12 18 1 6 0 0 0 12 19 1 0 0 0 0 13 19 1 6 0 0 0 14 20 1 6 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 1 0 0 0 16 20 1 0 0 0 0 16 24 2 0 0 0 0 17 20 1 6 0 0 0 17 25 1 0 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 20 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.19
Volume:	356.292
LogP:	0.337
LogD:	0.473
LogS:	-2.956
# Rotatable Bonds:	1
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	6.32
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.857
MDCK Permeability:	2.738804505497683e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.164
Human Intestinal Absorption (HIA):	0.093
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.7
Plasma Protein Binding (PPB):	53.504066467285156%
Volume Distribution (VD):	1.046
Pgp-substrate:	53.283363342285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.744
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.482
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.381
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	4.175
Half-life (T1/2):	0.414

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.292
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.943
Carcinogencity:	0.561
Eye Corrosion:	0.08
Eye Irritation:	0.115
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC142352

Natural Product ID:	NPC142352
*Common Name:**	Alboatisins B
IUPAC Name:	n.a.
Synonyms:	alboatisins B
Standard InCHIKey:	NAJAPJJKLLFJJT-JFJWUTIJSA-N
Standard InCHI:	InChI=1S/C20H28O5/c1-10-11-7-13-19(3)6-4-5-18(2,9-21)12(19)8-14(22)20(13,16(10)24)17(25)15(11)23/h9,11-15,17,22-23,25H,1,4-8H2,2-3H3/t11-,12+,13-,14+,15-,17+,18+,19+,20-/m0/s1
SMILES:	C=C1[C@@H]2C[C@H]3[C@]4(C)CCC[C@](C)(C=O)[C@H]4C[C@H]([C@@]3(C1=O)[C@@H]([C@H]2O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228664
PubChem CID:	16737107
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003401] Villanovane, atisane, trachylobane or helvifulvane diterpenoids [CHEMONTID:0002738] Atisane diterpenoids

*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
NPO23065	Isodon albopilosus	Species	Lamiaceae	Eukaryota	aerial parts	Maoxian, Sichuan Province, China	2004-JUL	PMID[16378369]
NPO23065	Isodon albopilosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17497809]
NPO23065	Isodon albopilosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23065	Isodon albopilosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23065	Isodon albopilosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8300.0	nM	PMID[516884]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	7900.0	nM	PMID[516884]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	13600.0	nM	PMID[516884]

☑ 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 NPC142352 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	265
0.1-0.2	2070
0.2-0.3	6597
0.3-0.4	12541
0.4-0.5	10308
0.5-0.6	6129
0.6-0.7	3291
0.7-0.8	1383
0.8-0.85	109
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC41070
0.8925	High Similarity	NPC29112
0.8913	High Similarity	NPC59350
0.875	High Similarity	NPC127408
0.875	High Similarity	NPC291785
0.871	High Similarity	NPC59170
0.8696	High Similarity	NPC180849
0.8667	High Similarity	NPC34190
0.8632	High Similarity	NPC165616
0.8632	High Similarity	NPC135548
0.8632	High Similarity	NPC264979
0.8571	High Similarity	NPC174619
0.8526	High Similarity	NPC84018
0.8526	High Similarity	NPC138245
0.8526	High Similarity	NPC231060
0.8511	High Similarity	NPC144739
0.8511	High Similarity	NPC181594
0.8511	High Similarity	NPC82138
0.8495	Intermediate Similarity	NPC80401
0.8469	Intermediate Similarity	NPC60947
0.8421	Intermediate Similarity	NPC292374
0.8421	Intermediate Similarity	NPC153775
0.8421	Intermediate Similarity	NPC29247
0.8421	Intermediate Similarity	NPC261333
0.8421	Intermediate Similarity	NPC111524
0.8421	Intermediate Similarity	NPC129004
0.8421	Intermediate Similarity	NPC289539
0.8421	Intermediate Similarity	NPC191094
0.8421	Intermediate Similarity	NPC215271
0.8421	Intermediate Similarity	NPC91772
0.8421	Intermediate Similarity	NPC104371
0.8421	Intermediate Similarity	NPC101233
0.8421	Intermediate Similarity	NPC302008
0.8404	Intermediate Similarity	NPC278106
0.8404	Intermediate Similarity	NPC299185
0.8404	Intermediate Similarity	NPC476168
0.837	Intermediate Similarity	NPC165895
0.8367	Intermediate Similarity	NPC470388
0.8351	Intermediate Similarity	NPC170978
0.8333	Intermediate Similarity	NPC55973
0.8316	Intermediate Similarity	NPC472496
0.8298	Intermediate Similarity	NPC149761
0.8298	Intermediate Similarity	NPC470378
0.8298	Intermediate Similarity	NPC261994
0.828	Intermediate Similarity	NPC472739
0.8265	Intermediate Similarity	NPC29765
0.8265	Intermediate Similarity	NPC111214
0.8265	Intermediate Similarity	NPC271614
0.8247	Intermediate Similarity	NPC104568
0.8247	Intermediate Similarity	NPC13949
0.8247	Intermediate Similarity	NPC140242
0.8242	Intermediate Similarity	NPC146683
0.8235	Intermediate Similarity	NPC471461
0.8235	Intermediate Similarity	NPC67745
0.8229	Intermediate Similarity	NPC169751
0.8229	Intermediate Similarity	NPC272635
0.8218	Intermediate Similarity	NPC284865
0.82	Intermediate Similarity	NPC272472
0.8182	Intermediate Similarity	NPC35239
0.8173	Intermediate Similarity	NPC471093
0.8173	Intermediate Similarity	NPC473324
0.8173	Intermediate Similarity	NPC100908
0.8172	Intermediate Similarity	NPC153604
0.8172	Intermediate Similarity	NPC57469
0.8172	Intermediate Similarity	NPC259009
0.8163	Intermediate Similarity	NPC106112
0.8163	Intermediate Similarity	NPC261935
0.8155	Intermediate Similarity	NPC89860
0.8155	Intermediate Similarity	NPC218123
0.8155	Intermediate Similarity	NPC112895
0.8155	Intermediate Similarity	NPC273155
0.8155	Intermediate Similarity	NPC231278
0.8155	Intermediate Similarity	NPC189663
0.8155	Intermediate Similarity	NPC63841
0.8152	Intermediate Similarity	NPC102292
0.8137	Intermediate Similarity	NPC130511
0.8137	Intermediate Similarity	NPC307660
0.8132	Intermediate Similarity	NPC118800
0.8132	Intermediate Similarity	NPC291320
0.8132	Intermediate Similarity	NPC471036
0.8119	Intermediate Similarity	NPC277074
0.8119	Intermediate Similarity	NPC209298
0.8111	Intermediate Similarity	NPC328264
0.81	Intermediate Similarity	NPC148279
0.8095	Intermediate Similarity	NPC122339
0.8095	Intermediate Similarity	NPC29505
0.8081	Intermediate Similarity	NPC109059
0.8081	Intermediate Similarity	NPC188833
0.8081	Intermediate Similarity	NPC288
0.8077	Intermediate Similarity	NPC118721
0.8077	Intermediate Similarity	NPC252679
0.8065	Intermediate Similarity	NPC269396
0.8065	Intermediate Similarity	NPC98236
0.8061	Intermediate Similarity	NPC73004
0.8061	Intermediate Similarity	NPC201657
0.8061	Intermediate Similarity	NPC469545
0.8061	Intermediate Similarity	NPC204961
0.8061	Intermediate Similarity	NPC5532
0.8061	Intermediate Similarity	NPC173744
0.8061	Intermediate Similarity	NPC61369
0.8061	Intermediate Similarity	NPC473158
0.8058	Intermediate Similarity	NPC186054
0.8058	Intermediate Similarity	NPC166993
0.8041	Intermediate Similarity	NPC64006
0.8021	Intermediate Similarity	NPC211403
0.8021	Intermediate Similarity	NPC198242
0.8021	Intermediate Similarity	NPC99380
0.8021	Intermediate Similarity	NPC250753
0.802	Intermediate Similarity	NPC309388
0.802	Intermediate Similarity	NPC475803
0.8019	Intermediate Similarity	NPC471245
0.8019	Intermediate Similarity	NPC473303
0.8	Intermediate Similarity	NPC156324
0.8	Intermediate Similarity	NPC471476
0.8	Intermediate Similarity	NPC55503
0.8	Intermediate Similarity	NPC69627
0.7981	Intermediate Similarity	NPC473410
0.7981	Intermediate Similarity	NPC471094
0.7981	Intermediate Similarity	NPC469984
0.798	Intermediate Similarity	NPC187933
0.798	Intermediate Similarity	NPC247139
0.798	Intermediate Similarity	NPC9613
0.7961	Intermediate Similarity	NPC200957
0.7961	Intermediate Similarity	NPC138908
0.7959	Intermediate Similarity	NPC96916
0.7959	Intermediate Similarity	NPC210214
0.7957	Intermediate Similarity	NPC190704
0.7957	Intermediate Similarity	NPC471034
0.7944	Intermediate Similarity	NPC471248
0.7944	Intermediate Similarity	NPC471252
0.7941	Intermediate Similarity	NPC225238
0.7941	Intermediate Similarity	NPC122811
0.7941	Intermediate Similarity	NPC96217
0.7941	Intermediate Similarity	NPC139347
0.7941	Intermediate Similarity	NPC87927
0.7938	Intermediate Similarity	NPC294263
0.7925	Intermediate Similarity	NPC63244
0.7925	Intermediate Similarity	NPC471243
0.7925	Intermediate Similarity	NPC213320
0.7921	Intermediate Similarity	NPC471790
0.7921	Intermediate Similarity	NPC14634
0.7921	Intermediate Similarity	NPC52899
0.7921	Intermediate Similarity	NPC46848
0.7921	Intermediate Similarity	NPC289148
0.7921	Intermediate Similarity	NPC163963
0.7917	Intermediate Similarity	NPC169933
0.7905	Intermediate Similarity	NPC102741
0.79	Intermediate Similarity	NPC471038
0.79	Intermediate Similarity	NPC26270
0.7895	Intermediate Similarity	NPC206060
0.7895	Intermediate Similarity	NPC474925
0.7895	Intermediate Similarity	NPC158778
0.7889	Intermediate Similarity	NPC476812
0.7885	Intermediate Similarity	NPC78966
0.7885	Intermediate Similarity	NPC471474
0.7885	Intermediate Similarity	NPC284732
0.7879	Intermediate Similarity	NPC259733
0.7879	Intermediate Similarity	NPC219353
0.7879	Intermediate Similarity	NPC223169
0.7879	Intermediate Similarity	NPC256227
0.7879	Intermediate Similarity	NPC207922
0.7879	Intermediate Similarity	NPC158371
0.7879	Intermediate Similarity	NPC132824
0.7865	Intermediate Similarity	NPC149249
0.7864	Intermediate Similarity	NPC301787
0.7864	Intermediate Similarity	NPC475036
0.7864	Intermediate Similarity	NPC13149
0.7857	Intermediate Similarity	NPC20235
0.7857	Intermediate Similarity	NPC277399
0.7857	Intermediate Similarity	NPC280804
0.7857	Intermediate Similarity	NPC32407
0.7857	Intermediate Similarity	NPC88116
0.7857	Intermediate Similarity	NPC474529
0.7857	Intermediate Similarity	NPC263548
0.7857	Intermediate Similarity	NPC222047
0.7857	Intermediate Similarity	NPC470386
0.7857	Intermediate Similarity	NPC282395
0.7857	Intermediate Similarity	NPC209868
0.7857	Intermediate Similarity	NPC470385
0.7857	Intermediate Similarity	NPC299996
0.7857	Intermediate Similarity	NPC231063
0.7857	Intermediate Similarity	NPC145667
0.785	Intermediate Similarity	NPC473397
0.785	Intermediate Similarity	NPC471244
0.785	Intermediate Similarity	NPC145625
0.785	Intermediate Similarity	NPC473352
0.785	Intermediate Similarity	NPC474927
0.7849	Intermediate Similarity	NPC474482
0.7849	Intermediate Similarity	NPC264665
0.7849	Intermediate Similarity	NPC475745
0.7849	Intermediate Similarity	NPC74595
0.7843	Intermediate Similarity	NPC286519
0.7843	Intermediate Similarity	NPC88203
0.7843	Intermediate Similarity	NPC304832
0.7843	Intermediate Similarity	NPC275990
0.7843	Intermediate Similarity	NPC246736
0.7843	Intermediate Similarity	NPC214946
0.7843	Intermediate Similarity	NPC148628
0.7843	Intermediate Similarity	NPC76866
0.7835	Intermediate Similarity	NPC155304

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 NPC142352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	2538
0.2-0.3	3961
0.3-0.4	1584
0.4-0.5	457
0.5-0.6	188
0.6-0.7	128
0.7-0.8	9
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
0.7525	Intermediate Similarity	NPD4697	Phase 3
0.7475	Intermediate Similarity	NPD7515	Phase 2
0.7396	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4634	Approved
0.732	Intermediate Similarity	NPD3618	Phase 1
0.7308	Intermediate Similarity	NPD5285	Approved
0.7308	Intermediate Similarity	NPD4696	Approved
0.7308	Intermediate Similarity	NPD5286	Approved
0.73	Intermediate Similarity	NPD8034	Phase 2
0.73	Intermediate Similarity	NPD6079	Approved
0.73	Intermediate Similarity	NPD8035	Phase 2
0.7282	Intermediate Similarity	NPD4755	Approved
0.7282	Intermediate Similarity	NPD7902	Approved
0.7273	Intermediate Similarity	NPD5328	Approved
0.7184	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5221	Approved
0.7184	Intermediate Similarity	NPD5222	Approved
0.717	Intermediate Similarity	NPD5225	Approved
0.717	Intermediate Similarity	NPD5224	Approved
0.717	Intermediate Similarity	NPD4633	Approved
0.717	Intermediate Similarity	NPD5226	Approved
0.717	Intermediate Similarity	NPD5211	Phase 2
0.7157	Intermediate Similarity	NPD7748	Approved
0.7156	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4700	Approved
0.7115	Intermediate Similarity	NPD5173	Approved
0.7103	Intermediate Similarity	NPD5174	Approved
0.7103	Intermediate Similarity	NPD5175	Approved
0.7083	Intermediate Similarity	NPD3667	Approved
0.7075	Intermediate Similarity	NPD5223	Approved
0.7037	Intermediate Similarity	NPD5141	Approved
0.7034	Intermediate Similarity	NPD8328	Phase 3
0.701	Intermediate Similarity	NPD4788	Approved
0.699	Remote Similarity	NPD7900	Approved
0.699	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7115	Discovery
0.6939	Remote Similarity	NPD4786	Approved
0.6909	Remote Similarity	NPD5697	Approved
0.6893	Remote Similarity	NPD4202	Approved
0.6887	Remote Similarity	NPD4225	Approved
0.6882	Remote Similarity	NPD3703	Phase 2
0.6847	Remote Similarity	NPD4730	Approved
0.6847	Remote Similarity	NPD4729	Approved
0.6847	Remote Similarity	NPD5128	Approved
0.6847	Remote Similarity	NPD6899	Approved
0.6847	Remote Similarity	NPD6881	Approved
0.6818	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD4767	Approved
0.6818	Remote Similarity	NPD6675	Approved
0.6818	Remote Similarity	NPD7128	Approved
0.6818	Remote Similarity	NPD4768	Approved
0.6814	Remote Similarity	NPD6649	Approved
0.6814	Remote Similarity	NPD6650	Approved
0.6789	Remote Similarity	NPD4754	Approved
0.6786	Remote Similarity	NPD6373	Approved
0.6786	Remote Similarity	NPD6012	Approved
0.6786	Remote Similarity	NPD6372	Approved
0.6786	Remote Similarity	NPD6013	Approved
0.6786	Remote Similarity	NPD6014	Approved
0.678	Remote Similarity	NPD6319	Approved
0.6771	Remote Similarity	NPD7645	Phase 2
0.6768	Remote Similarity	NPD3665	Phase 1
0.6768	Remote Similarity	NPD3666	Approved
0.6768	Remote Similarity	NPD3133	Approved
0.6757	Remote Similarity	NPD5701	Approved
0.6754	Remote Similarity	NPD8297	Approved
0.6731	Remote Similarity	NPD6399	Phase 3
0.6726	Remote Similarity	NPD7102	Approved
0.6726	Remote Similarity	NPD6883	Approved
0.6726	Remote Similarity	NPD5250	Approved
0.6726	Remote Similarity	NPD5247	Approved
0.6726	Remote Similarity	NPD5248	Approved
0.6726	Remote Similarity	NPD5249	Phase 3
0.6726	Remote Similarity	NPD7290	Approved
0.6726	Remote Similarity	NPD5251	Approved
0.6703	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4695	Discontinued
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD4632	Approved
0.6696	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6637	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6411	Approved
0.6613	Remote Similarity	NPD7319	Approved
0.6609	Remote Similarity	NPD6882	Approved
0.6604	Remote Similarity	NPD5210	Approved
0.6604	Remote Similarity	NPD4629	Approved
0.6602	Remote Similarity	NPD4753	Phase 2
0.66	Remote Similarity	NPD3668	Phase 3
0.6583	Remote Similarity	NPD6015	Approved
0.6583	Remote Similarity	NPD6016	Approved
0.6579	Remote Similarity	NPD5169	Approved
0.6579	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5135	Approved
0.6569	Remote Similarity	NPD3573	Approved
0.6562	Remote Similarity	NPD6116	Phase 1
0.6559	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5168	Approved
0.6532	Remote Similarity	NPD7736	Approved
0.6531	Remote Similarity	NPD7525	Registered
0.6529	Remote Similarity	NPD6370	Approved
0.6529	Remote Similarity	NPD5988	Approved
0.6522	Remote Similarity	NPD5127	Approved
0.6504	Remote Similarity	NPD7507	Approved
0.65	Remote Similarity	NPD6059	Approved
0.646	Remote Similarity	NPD6412	Phase 2
0.6458	Remote Similarity	NPD6117	Approved
0.6446	Remote Similarity	NPD6921	Approved
0.6442	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6101	Approved
0.6441	Remote Similarity	NPD6274	Approved
0.6423	Remote Similarity	NPD7492	Approved
0.6387	Remote Similarity	NPD6009	Approved
0.6379	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6008	Approved
0.6371	Remote Similarity	NPD6616	Approved
0.6356	Remote Similarity	NPD5167	Approved
0.6348	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD3698	Phase 2
0.6327	Remote Similarity	NPD6697	Approved
0.6327	Remote Similarity	NPD6115	Approved
0.6327	Remote Similarity	NPD6118	Approved
0.6327	Remote Similarity	NPD6114	Approved
0.632	Remote Similarity	NPD7078	Approved
0.6311	Remote Similarity	NPD5279	Phase 3
0.6296	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7101	Approved
0.6281	Remote Similarity	NPD7100	Approved
0.6277	Remote Similarity	NPD4244	Approved
0.6277	Remote Similarity	NPD4245	Approved
0.6273	Remote Similarity	NPD7638	Approved
0.6271	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6317	Approved
0.6238	Remote Similarity	NPD4223	Phase 3
0.6238	Remote Similarity	NPD4221	Approved
0.6216	Remote Similarity	NPD7639	Approved
0.6216	Remote Similarity	NPD7640	Approved
0.6198	Remote Similarity	NPD6335	Approved
0.6198	Remote Similarity	NPD6314	Approved
0.6198	Remote Similarity	NPD6313	Approved
0.619	Remote Similarity	NPD8293	Discontinued
0.619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6083	Phase 2
0.6182	Remote Similarity	NPD6084	Phase 2
0.6179	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5983	Phase 2
0.617	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6868	Approved
0.6162	Remote Similarity	NPD3617	Approved
0.6162	Remote Similarity	NPD3671	Phase 1
0.6154	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4522	Approved
0.6126	Remote Similarity	NPD5696	Approved
0.6122	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6686	Approved
0.6117	Remote Similarity	NPD4197	Approved
0.6111	Remote Similarity	NPD5778	Approved
0.6111	Remote Similarity	NPD5779	Approved
0.6105	Remote Similarity	NPD4789	Approved
0.6091	Remote Similarity	NPD7614	Phase 1
0.6087	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.608	Remote Similarity	NPD7604	Phase 2
0.6064	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5360	Phase 3
0.6058	Remote Similarity	NPD5329	Approved
0.6055	Remote Similarity	NPD5282	Discontinued
0.6048	Remote Similarity	NPD6909	Approved
0.6048	Remote Similarity	NPD6908	Approved
0.602	Remote Similarity	NPD6942	Approved
0.602	Remote Similarity	NPD7339	Approved
0.6019	Remote Similarity	NPD5281	Approved
0.6019	Remote Similarity	NPD5284	Approved
0.6016	Remote Similarity	NPD6033	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD4138	Approved
0.6	Remote Similarity	NPD5690	Phase 2
0.6	Remote Similarity	NPD5205	Approved
0.6	Remote Similarity	NPD4688	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD4693	Phase 3
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD4690	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