NPASS Compound

Structure

NPC472234 OpenBabel07101719512D 37 43 0 0 1 0 0 0 0 0999 V2000 -2.4811 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4584 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0906 -5.0017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7556 -4.3821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7329 -4.3821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2564 -2.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2564 0.2888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5516 -3.5358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7052 -3.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0906 -2.0699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2443 -1.5813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9294 -1.8833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7052 -0.1154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5516 -0.6040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3550 -1.0926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9294 0.6753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9294 1.2793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3979 -1.0926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5039 1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5039 0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9369 -4.5131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3979 -3.0472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7052 -2.0699 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0906 -3.0472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9294 2.2565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2443 -3.5358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8589 -1.5813 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8589 -0.6040 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3979 -2.0699 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5516 -1.5813 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9294 -0.3020 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7833 -5.0017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2314 3.1860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9369 -3.5358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9545 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 20 1 0 0 0 0 3 21 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 29 1 0 0 0 0 12 15 1 0 0 0 0 12 27 1 0 0 0 0 13 14 1 0 0 0 0 13 28 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 31 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 0 0 0 19 25 1 0 0 0 0 20 32 1 1 0 0 0 21 33 2 0 0 0 0 21 35 1 0 0 0 0 22 26 1 0 0 0 0 22 29 1 6 0 0 0 23 27 1 6 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 1 0 0 0 25 34 2 0 0 0 0 25 36 1 0 0 0 0 27 28 1 1 0 0 0 28 32 1 1 0 0 0 29 30 1 1 0 0 0 30 14 1 6 0 0 0 31 16 1 1 0 0 0 31 36 1 0 0 0 0 31 37 1 0 0 0 0 32 15 1 1 0 0 0 32 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.36
Volume:	643.065
LogP:	4.412
LogD:	4.061
LogS:	-5.359
# Rotatable Bonds:	4
TPSA:	91.43
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	6.333
Fsp3:	0.763
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.244
MDCK Permeability:	1.982009780476801e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.162

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.516
Plasma Protein Binding (PPB):	88.21073913574219%
Volume Distribution (VD):	1.201
Pgp-substrate:	4.650792598724365%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.453
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.67
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.945
CYP3A4-substrate:	0.945

ADMET: Excretion

Clearance (CL):	12.256
Half-life (T1/2):	0.431

ADMET: Toxicity

hERG Blockers:	0.666
Human Hepatotoxicity (H-HT):	0.648
Drug-inuced Liver Injury (DILI):	0.701
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.416
Carcinogencity:	0.656
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC472234

Natural Product ID:	NPC472234
*Common Name:**	ACMCWGMBFMGKAF-ZEFOCKMKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ACMCWGMBFMGKAF-ZEFOCKMKSA-N
Standard InCHI:	InChI=1S/C32H48O5/c1-19-16-31(36-25(19)34)17-20(2)32(37-31)15-12-27(6)23-9-8-22-26(4,5)24(35-21(3)33)10-11-29(22)18-30(23,29)14-13-28(27,32)7/h19-20,22-24H,8-18H2,1-7H3/t19-,20-,22+,23-,24-,27+,28+,29-,30-,31+,32-/m1/s1
SMILES:	CC1CC2(CC(C3(O2)CCC4(C3(CCC56C4CCC7C5(C6)CCC(C7(C)C)OC(=O)C)C)C)C)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3353851
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO33399	abies faxoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25554367]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	9800.0	nM	PMID[473161]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	10700.0	nM	PMID[473161]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7500.0	nM	PMID[473161]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[473161]

☑ 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 NPC472234 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	500
0.1-0.2	4727
0.2-0.3	15679
0.3-0.4	8398
0.4-0.5	5699
0.5-0.6	5689
0.6-0.7	1735
0.7-0.8	256
0.8-0.85	7
0.85-0.9	2
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472233
0.9425	High Similarity	NPC472231
0.9425	High Similarity	NPC472232
0.881	High Similarity	NPC472229
0.881	High Similarity	NPC472230
0.8276	Intermediate Similarity	NPC13494
0.8247	Intermediate Similarity	NPC244969
0.8247	Intermediate Similarity	NPC213528
0.8182	Intermediate Similarity	NPC306776
0.8161	Intermediate Similarity	NPC58631
0.8081	Intermediate Similarity	NPC100078
0.8	Intermediate Similarity	NPC166079
0.7979	Intermediate Similarity	NPC472237
0.7979	Intermediate Similarity	NPC472238
0.7935	Intermediate Similarity	NPC33398
0.7931	Intermediate Similarity	NPC73013
0.79	Intermediate Similarity	NPC472227
0.79	Intermediate Similarity	NPC472228
0.7889	Intermediate Similarity	NPC319909
0.7865	Intermediate Similarity	NPC24556
0.7857	Intermediate Similarity	NPC109510
0.7841	Intermediate Similarity	NPC261616
0.7791	Intermediate Similarity	NPC471046
0.7789	Intermediate Similarity	NPC256104
0.7789	Intermediate Similarity	NPC182740
0.7789	Intermediate Similarity	NPC211845
0.7789	Intermediate Similarity	NPC122083
0.7789	Intermediate Similarity	NPC161035
0.7789	Intermediate Similarity	NPC35164
0.7766	Intermediate Similarity	NPC77756
0.7765	Intermediate Similarity	NPC272359
0.7753	Intermediate Similarity	NPC12933
0.7742	Intermediate Similarity	NPC221993
0.7738	Intermediate Similarity	NPC197701
0.7732	Intermediate Similarity	NPC116683
0.7732	Intermediate Similarity	NPC156377
0.7732	Intermediate Similarity	NPC145553
0.7732	Intermediate Similarity	NPC476728
0.7727	Intermediate Similarity	NPC477287
0.7727	Intermediate Similarity	NPC474754
0.7708	Intermediate Similarity	NPC477495
0.7701	Intermediate Similarity	NPC207010
0.7701	Intermediate Similarity	NPC471151
0.7701	Intermediate Similarity	NPC317913
0.7701	Intermediate Similarity	NPC474404
0.7684	Intermediate Similarity	NPC52756
0.7684	Intermediate Similarity	NPC475878
0.7684	Intermediate Similarity	NPC474065
0.764	Intermediate Similarity	NPC134227
0.7629	Intermediate Similarity	NPC305808
0.7629	Intermediate Similarity	NPC21897
0.7629	Intermediate Similarity	NPC470031
0.7604	Intermediate Similarity	NPC228700
0.7586	Intermediate Similarity	NPC4209
0.7576	Intermediate Similarity	NPC292775
0.7558	Intermediate Similarity	NPC55508
0.7556	Intermediate Similarity	NPC474870
0.7556	Intermediate Similarity	NPC469745
0.7556	Intermediate Similarity	NPC271572
0.7528	Intermediate Similarity	NPC476176
0.7528	Intermediate Similarity	NPC80891
0.7528	Intermediate Similarity	NPC201276
0.7527	Intermediate Similarity	NPC472272
0.7526	Intermediate Similarity	NPC472224
0.7526	Intermediate Similarity	NPC472223
0.7526	Intermediate Similarity	NPC470424
0.75	Intermediate Similarity	NPC470030
0.75	Intermediate Similarity	NPC473066
0.75	Intermediate Similarity	NPC474996
0.75	Intermediate Similarity	NPC475031
0.75	Intermediate Similarity	NPC41843
0.75	Intermediate Similarity	NPC65133
0.7477	Intermediate Similarity	NPC97002
0.7475	Intermediate Similarity	NPC266417
0.7473	Intermediate Similarity	NPC477286
0.7473	Intermediate Similarity	NPC61107
0.7473	Intermediate Similarity	NPC477284
0.7473	Intermediate Similarity	NPC289486
0.7473	Intermediate Similarity	NPC286719
0.7471	Intermediate Similarity	NPC72444
0.7471	Intermediate Similarity	NPC212733
0.7453	Intermediate Similarity	NPC473062
0.7447	Intermediate Similarity	NPC210658
0.7447	Intermediate Similarity	NPC161928
0.7447	Intermediate Similarity	NPC252714
0.7444	Intermediate Similarity	NPC125366
0.7444	Intermediate Similarity	NPC472853
0.7442	Intermediate Similarity	NPC474123
0.7429	Intermediate Similarity	NPC227879
0.7429	Intermediate Similarity	NPC208333
0.7426	Intermediate Similarity	NPC178853
0.7426	Intermediate Similarity	NPC476512
0.7426	Intermediate Similarity	NPC108227
0.7426	Intermediate Similarity	NPC472081
0.7423	Intermediate Similarity	NPC472226
0.7423	Intermediate Similarity	NPC472225
0.7423	Intermediate Similarity	NPC476189
0.7419	Intermediate Similarity	NPC98270
0.7416	Intermediate Similarity	NPC224802
0.7416	Intermediate Similarity	NPC476732
0.7416	Intermediate Similarity	NPC171426
0.7416	Intermediate Similarity	NPC471045
0.7416	Intermediate Similarity	NPC80089
0.7416	Intermediate Similarity	NPC199965
0.7416	Intermediate Similarity	NPC324700
0.7416	Intermediate Similarity	NPC34046
0.7407	Intermediate Similarity	NPC79193
0.7396	Intermediate Similarity	NPC470114
0.7391	Intermediate Similarity	NPC477285
0.7391	Intermediate Similarity	NPC259173
0.7391	Intermediate Similarity	NPC111582
0.7374	Intermediate Similarity	NPC475765
0.7374	Intermediate Similarity	NPC475785
0.7368	Intermediate Similarity	NPC128475
0.7363	Intermediate Similarity	NPC190940
0.7363	Intermediate Similarity	NPC48756
0.7363	Intermediate Similarity	NPC280781
0.7356	Intermediate Similarity	NPC167702
0.7356	Intermediate Similarity	NPC280026
0.7353	Intermediate Similarity	NPC470029
0.7353	Intermediate Similarity	NPC134967
0.7353	Intermediate Similarity	NPC310138
0.7353	Intermediate Similarity	NPC114700
0.7349	Intermediate Similarity	NPC84562
0.7347	Intermediate Similarity	NPC470423
0.7347	Intermediate Similarity	NPC206878
0.734	Intermediate Similarity	NPC92139
0.734	Intermediate Similarity	NPC474008
0.734	Intermediate Similarity	NPC474448
0.7339	Intermediate Similarity	NPC475490
0.7333	Intermediate Similarity	NPC320144
0.7333	Intermediate Similarity	NPC472079
0.7327	Intermediate Similarity	NPC108371
0.7326	Intermediate Similarity	NPC469940
0.732	Intermediate Similarity	NPC160506
0.7312	Intermediate Similarity	NPC473336
0.7312	Intermediate Similarity	NPC475509
0.7312	Intermediate Similarity	NPC51135
0.7312	Intermediate Similarity	NPC82492
0.7312	Intermediate Similarity	NPC471044
0.7312	Intermediate Similarity	NPC25802
0.7312	Intermediate Similarity	NPC101138
0.7312	Intermediate Similarity	NPC473299
0.7303	Intermediate Similarity	NPC298168
0.7303	Intermediate Similarity	NPC180199
0.7303	Intermediate Similarity	NPC307865
0.7303	Intermediate Similarity	NPC212453
0.7303	Intermediate Similarity	NPC143133
0.7303	Intermediate Similarity	NPC477919
0.73	Intermediate Similarity	NPC471241
0.73	Intermediate Similarity	NPC469810
0.729	Intermediate Similarity	NPC470311
0.7283	Intermediate Similarity	NPC242771
0.7283	Intermediate Similarity	NPC100366
0.7283	Intermediate Similarity	NPC164289
0.7283	Intermediate Similarity	NPC311642
0.7283	Intermediate Similarity	NPC477935
0.7283	Intermediate Similarity	NPC470611
0.7283	Intermediate Similarity	NPC296734
0.7283	Intermediate Similarity	NPC477936
0.7283	Intermediate Similarity	NPC121121
0.7282	Intermediate Similarity	NPC139181
0.7282	Intermediate Similarity	NPC97260
0.7282	Intermediate Similarity	NPC476837
0.7273	Intermediate Similarity	NPC478105
0.7273	Intermediate Similarity	NPC215570
0.7273	Intermediate Similarity	NPC273366
0.7255	Intermediate Similarity	NPC477172
0.7253	Intermediate Similarity	NPC1882
0.7253	Intermediate Similarity	NPC170038
0.7253	Intermediate Similarity	NPC471216
0.7253	Intermediate Similarity	NPC471217
0.7253	Intermediate Similarity	NPC475456
0.7253	Intermediate Similarity	NPC477851
0.7241	Intermediate Similarity	NPC474755
0.7228	Intermediate Similarity	NPC473155
0.7228	Intermediate Similarity	NPC472144
0.7222	Intermediate Similarity	NPC478128
0.7222	Intermediate Similarity	NPC31031
0.7222	Intermediate Similarity	NPC329117
0.7222	Intermediate Similarity	NPC185465
0.7222	Intermediate Similarity	NPC243594
0.7222	Intermediate Similarity	NPC477489
0.7212	Intermediate Similarity	NPC88469
0.7212	Intermediate Similarity	NPC327093
0.7204	Intermediate Similarity	NPC327451
0.7204	Intermediate Similarity	NPC15821
0.72	Intermediate Similarity	NPC193785
0.7188	Intermediate Similarity	NPC56777
0.7188	Intermediate Similarity	NPC4309
0.7188	Intermediate Similarity	NPC201607
0.7188	Intermediate Similarity	NPC471221
0.7174	Intermediate Similarity	NPC71541
0.7174	Intermediate Similarity	NPC77311
0.7174	Intermediate Similarity	NPC73515
0.7172	Intermediate Similarity	NPC175
0.7172	Intermediate Similarity	NPC151214
0.7172	Intermediate Similarity	NPC191915
0.7158	Intermediate Similarity	NPC80700
0.7158	Intermediate Similarity	NPC477283

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 NPC472234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	503
0.1-0.2	4277
0.2-0.3	3155
0.3-0.4	677
0.4-0.5	253
0.5-0.6	211
0.6-0.7	62
0.7-0.8	12
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
0.7738	Intermediate Similarity	NPD5777	Approved
0.7701	Intermediate Similarity	NPD6116	Phase 1
0.7586	Intermediate Similarity	NPD6117	Approved
0.7416	Intermediate Similarity	NPD6115	Approved
0.7416	Intermediate Similarity	NPD6118	Approved
0.7416	Intermediate Similarity	NPD6114	Approved
0.7416	Intermediate Similarity	NPD6697	Approved
0.7356	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8035	Phase 2
0.732	Intermediate Similarity	NPD8034	Phase 2
0.7273	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3702	Approved
0.7065	Intermediate Similarity	NPD6928	Phase 2
0.7048	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6008	Approved
0.6932	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1700	Approved
0.6832	Remote Similarity	NPD6001	Approved
0.6818	Remote Similarity	NPD4244	Approved
0.6818	Remote Similarity	NPD4245	Approved
0.6782	Remote Similarity	NPD5360	Phase 3
0.6782	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6081	Approved
0.6705	Remote Similarity	NPD3698	Phase 2
0.6705	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6882	Approved
0.6591	Remote Similarity	NPD229	Approved
0.6569	Remote Similarity	NPD6399	Phase 3
0.6569	Remote Similarity	NPD8171	Discontinued
0.6552	Remote Similarity	NPD4224	Phase 2
0.6545	Remote Similarity	NPD7320	Approved
0.6522	Remote Similarity	NPD3703	Phase 2
0.6514	Remote Similarity	NPD6675	Approved
0.6514	Remote Similarity	NPD6402	Approved
0.6514	Remote Similarity	NPD7128	Approved
0.6514	Remote Similarity	NPD5739	Approved
0.6505	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7900	Approved
0.65	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6903	Approved
0.6486	Remote Similarity	NPD6373	Approved
0.6486	Remote Similarity	NPD6372	Approved
0.6465	Remote Similarity	NPD6684	Approved
0.6465	Remote Similarity	NPD7146	Approved
0.6465	Remote Similarity	NPD5330	Approved
0.6465	Remote Similarity	NPD7521	Approved
0.6465	Remote Similarity	NPD7334	Approved
0.6465	Remote Similarity	NPD6409	Approved
0.6458	Remote Similarity	NPD1779	Approved
0.6458	Remote Similarity	NPD1780	Approved
0.6444	Remote Similarity	NPD4789	Approved
0.6442	Remote Similarity	NPD7991	Discontinued
0.6404	Remote Similarity	NPD8133	Approved
0.6396	Remote Similarity	NPD6881	Approved
0.6396	Remote Similarity	NPD6899	Approved
0.6393	Remote Similarity	NPD7736	Approved
0.6374	Remote Similarity	NPD4758	Discontinued
0.6372	Remote Similarity	NPD6650	Approved
0.6372	Remote Similarity	NPD6649	Approved
0.6372	Remote Similarity	NPD8130	Phase 1
0.6333	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7902	Approved
0.6316	Remote Similarity	NPD5364	Discontinued
0.6316	Remote Similarity	NPD8297	Approved
0.6311	Remote Similarity	NPD7078	Approved
0.6311	Remote Similarity	NPD8293	Discontinued
0.6306	Remote Similarity	NPD5701	Approved
0.6306	Remote Similarity	NPD5697	Approved
0.63	Remote Similarity	NPD6098	Approved
0.6283	Remote Similarity	NPD6883	Approved
0.6283	Remote Similarity	NPD7290	Approved
0.6283	Remote Similarity	NPD7102	Approved
0.6281	Remote Similarity	NPD7492	Approved
0.6275	Remote Similarity	NPD6080	Approved
0.6275	Remote Similarity	NPD6904	Approved
0.6275	Remote Similarity	NPD6673	Approved
0.6264	Remote Similarity	NPD4787	Phase 1
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7507	Approved
0.623	Remote Similarity	NPD6616	Approved
0.6228	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6617	Approved
0.6228	Remote Similarity	NPD6869	Approved
0.6228	Remote Similarity	NPD6847	Approved
0.6218	Remote Similarity	NPD6059	Approved
0.6218	Remote Similarity	NPD6054	Approved
0.6214	Remote Similarity	NPD5207	Approved
0.6204	Remote Similarity	NPD8418	Phase 2
0.6195	Remote Similarity	NPD6014	Approved
0.6195	Remote Similarity	NPD6013	Approved
0.6195	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD7748	Approved
0.6176	Remote Similarity	NPD6672	Approved
0.6176	Remote Similarity	NPD5737	Approved
0.6168	Remote Similarity	NPD6084	Phase 2
0.6168	Remote Similarity	NPD6083	Phase 2
0.6162	Remote Similarity	NPD4788	Approved
0.6146	Remote Similarity	NPD4238	Approved
0.6146	Remote Similarity	NPD3671	Phase 1
0.6146	Remote Similarity	NPD4802	Phase 2
0.6116	Remote Similarity	NPD6370	Approved
0.6111	Remote Similarity	NPD5696	Approved
0.6111	Remote Similarity	NPD7638	Approved
0.6102	Remote Similarity	NPD6009	Approved
0.6095	Remote Similarity	NPD4202	Approved
0.608	Remote Similarity	NPD7319	Approved
0.6055	Remote Similarity	NPD7639	Approved
0.6055	Remote Similarity	NPD7640	Approved
0.6053	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6052	Approved
0.6033	Remote Similarity	NPD6016	Approved
0.6033	Remote Similarity	NPD6015	Approved
0.6033	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4755	Approved
0.6019	Remote Similarity	NPD5208	Approved
0.6017	Remote Similarity	NPD6940	Discontinued
0.6	Remote Similarity	NPD3669	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD5693	Phase 1
0.6	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD5988	Approved
0.5982	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5695	Phase 3
0.5962	Remote Similarity	NPD6051	Approved
0.595	Remote Similarity	NPD8294	Approved
0.595	Remote Similarity	NPD8377	Approved
0.5946	Remote Similarity	NPD7632	Discontinued
0.5935	Remote Similarity	NPD7604	Phase 2
0.5917	Remote Similarity	NPD7328	Approved
0.5917	Remote Similarity	NPD7327	Approved
0.5917	Remote Similarity	NPD6335	Approved
0.5909	Remote Similarity	NPD5285	Approved
0.5909	Remote Similarity	NPD5286	Approved
0.5909	Remote Similarity	NPD4696	Approved
0.5909	Remote Similarity	NPD4700	Approved
0.5905	Remote Similarity	NPD5692	Phase 3
0.5902	Remote Similarity	NPD8033	Approved
0.5902	Remote Similarity	NPD8380	Approved
0.5902	Remote Similarity	NPD8379	Approved
0.5902	Remote Similarity	NPD8378	Approved
0.5902	Remote Similarity	NPD8296	Approved
0.5902	Remote Similarity	NPD8335	Approved
0.5882	Remote Similarity	NPD6274	Approved
0.5877	Remote Similarity	NPD6412	Phase 2
0.5877	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD6033	Approved
0.5872	Remote Similarity	NPD5959	Approved
0.5868	Remote Similarity	NPD7101	Approved
0.5868	Remote Similarity	NPD7100	Approved
0.5868	Remote Similarity	NPD7516	Approved
0.5862	Remote Similarity	NPD3198	Approved
0.5859	Remote Similarity	NPD7525	Registered
0.5856	Remote Similarity	NPD5223	Approved
0.5849	Remote Similarity	NPD5281	Approved
0.5849	Remote Similarity	NPD7515	Phase 2
0.5849	Remote Similarity	NPD5284	Approved
0.5849	Remote Similarity	NPD5694	Approved
0.5847	Remote Similarity	NPD4632	Approved
0.5833	Remote Similarity	NPD6317	Approved
0.5833	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7115	Discovery
0.5825	Remote Similarity	NPD3618	Phase 1
0.581	Remote Similarity	NPD5328	Approved
0.5806	Remote Similarity	NPD6067	Discontinued
0.5804	Remote Similarity	NPD5211	Phase 2
0.5804	Remote Similarity	NPD5225	Approved
0.5804	Remote Similarity	NPD5224	Approved
0.5804	Remote Similarity	NPD5226	Approved
0.5804	Remote Similarity	NPD4633	Approved
0.5789	Remote Similarity	NPD8040	Discontinued
0.5785	Remote Similarity	NPD6314	Approved
0.5785	Remote Similarity	NPD6313	Approved
0.5784	Remote Similarity	NPD4786	Approved
0.5772	Remote Similarity	NPD6908	Approved
0.5772	Remote Similarity	NPD6909	Approved
0.5752	Remote Similarity	NPD5175	Approved
0.5752	Remote Similarity	NPD4754	Approved
0.5752	Remote Similarity	NPD5174	Approved
0.5726	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5141	Approved
0.5701	Remote Similarity	NPD6079	Approved
0.5691	Remote Similarity	NPD6319	Approved
0.569	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD5654	Approved
0.5673	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4753	Phase 2
0.5652	Remote Similarity	NPD4767	Approved
0.5652	Remote Similarity	NPD4768	Approved
0.5652	Remote Similarity	NPD6920	Discontinued
0.5645	Remote Similarity	NPD5983	Phase 2
0.5641	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4697	Phase 3
0.5631	Remote Similarity	NPD3666	Approved
0.5631	Remote Similarity	NPD3665	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