NPASS Compound

Structure

NPC180733 OpenBabel07101718222D 38 42 0 0 1 0 0 0 0 0999 V2000 6.8437 0.7386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1309 1.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5054 2.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1527 1.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4836 2.4328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7926 3.3838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 3.4980 4.4543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2109 3.2953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 3 27 1 0 0 0 0 6 38 1 0 0 0 0 7 8 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 28 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 30 1 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 18 7 1 6 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 27 1 1 0 0 0 20 32 1 1 0 0 0 21 28 1 6 0 0 0 21 30 1 0 0 0 0 22 29 1 1 0 0 0 22 31 1 0 0 0 0 23 29 1 1 0 0 0 23 33 1 0 0 0 0 24 31 1 6 0 0 0 24 34 1 0 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 26 29 1 0 0 0 0 26 37 2 0 0 0 0 26 38 1 0 0 0 0 27 28 1 1 0 0 0 28 4 1 6 0 0 0 29 5 1 1 0 0 0 30 31 1 6 0 0 0 31 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.34
Volume:	555.572
LogP:	2.027
LogD:	1.924
LogS:	-4.417
# Rotatable Bonds:	8
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	6.138
Fsp3:	0.871
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:	-5.838
MDCK Permeability:	8.34649290482048e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.108
30% Bioavailability (F30%):	0.644

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.501
Plasma Protein Binding (PPB):	77.16633605957031%
Volume Distribution (VD):	0.35
Pgp-substrate:	14.192466735839844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.753
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.18
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.505
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	3.37
Half-life (T1/2):	0.515

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.638
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.823
Carcinogencity:	0.757
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC180733

Natural Product ID:	NPC180733
*Common Name:**	KALMVCDXDQYBPA-WQXOJWCKSA-N
IUPAC Name:	n.a.
Synonyms:	24-Epiquadrangularic Acid G
Standard InCHIKey:	KALMVCDXDQYBPA-WQXOJWCKSA-N
Standard InCHI:	InChI=1S/C31H48O7/c1-17(2)20(32)8-7-18(25(35)36)19-11-12-28(4)21-9-10-22-29(5,26(37)38-6)23(33)15-24(34)31(22)16-30(21,31)14-13-27(19,28)3/h18-24,32-34H,1,7-16H2,2-6H3,(H,35,36)/t18-,19-,20-,21+,22+,23+,24+,27-,28+,29+,30+,31-/m1/s1
SMILES:	COC(=O)[C@]1(C)[C@@H](O)C[C@@H]([C@]23[C@H]1CC[C@@H]1[C@@]3(C2)CC[C@]2([C@@]1(C)CC[C@@H]2[C@H](C(=O)O)CC[C@H](C(=C)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453000
PubChem CID:	10697557
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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	100.0	ug ml-1	PMID[501079]

☑ 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 NPC180733 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	220
0.1-0.2	1745
0.2-0.3	5691
0.3-0.4	11503
0.4-0.5	10067
0.5-0.6	5701
0.6-0.7	5589
0.7-0.8	1908
0.8-0.85	189
0.85-0.9	68
0.9-0.95	8
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC37047
1.0	High Similarity	NPC41971
0.9681	High Similarity	NPC75941
0.9574	High Similarity	NPC94906
0.9565	High Similarity	NPC288906
0.9565	High Similarity	NPC263135
0.9468	High Similarity	NPC472028
0.9375	High Similarity	NPC124544
0.9255	High Similarity	NPC234564
0.9072	High Similarity	NPC71706
0.901	High Similarity	NPC257082
0.899	High Similarity	NPC201763
0.898	High Similarity	NPC271980
0.898	High Similarity	NPC193934
0.8958	High Similarity	NPC469810
0.8947	High Similarity	NPC266431
0.8913	High Similarity	NPC146937
0.8911	High Similarity	NPC163216
0.89	High Similarity	NPC37600
0.8889	High Similarity	NPC312900
0.8878	High Similarity	NPC253886
0.8878	High Similarity	NPC121218
0.8878	High Similarity	NPC46848
0.8854	High Similarity	NPC329910
0.8842	High Similarity	NPC470385
0.8842	High Similarity	NPC470386
0.8835	High Similarity	NPC270586
0.8824	High Similarity	NPC285298
0.8812	High Similarity	NPC263729
0.8788	High Similarity	NPC88203
0.8788	High Similarity	NPC246736
0.8788	High Similarity	NPC214946
0.8788	High Similarity	NPC275990
0.8788	High Similarity	NPC148628
0.8788	High Similarity	NPC286519
0.8788	High Similarity	NPC304832
0.8788	High Similarity	NPC76866
0.8763	High Similarity	NPC253586
0.875	High Similarity	NPC470232
0.875	High Similarity	NPC470229
0.8713	High Similarity	NPC295366
0.87	High Similarity	NPC469985
0.8696	High Similarity	NPC302111
0.8687	High Similarity	NPC289148
0.8687	High Similarity	NPC52899
0.8687	High Similarity	NPC163963
0.8687	High Similarity	NPC295276
0.8673	High Similarity	NPC162459
0.8673	High Similarity	NPC28864
0.8673	High Similarity	NPC38296
0.8673	High Similarity	NPC38471
0.8673	High Similarity	NPC474793
0.8673	High Similarity	NPC471038
0.8673	High Similarity	NPC20479
0.8673	High Similarity	NPC98837
0.866	High Similarity	NPC470387
0.8646	High Similarity	NPC475118
0.8646	High Similarity	NPC469982
0.8646	High Similarity	NPC47853
0.8632	High Similarity	NPC198242
0.8632	High Similarity	NPC211403
0.8617	High Similarity	NPC213832
0.8617	High Similarity	NPC57954
0.8614	High Similarity	NPC47281
0.86	High Similarity	NPC170615
0.8586	High Similarity	NPC108371
0.8586	High Similarity	NPC293866
0.8586	High Similarity	NPC287676
0.8571	High Similarity	NPC190080
0.8571	High Similarity	NPC111187
0.8542	High Similarity	NPC287118
0.8542	High Similarity	NPC244356
0.8542	High Similarity	NPC224060
0.8542	High Similarity	NPC471902
0.8542	High Similarity	NPC473690
0.8529	High Similarity	NPC50535
0.8529	High Similarity	NPC200957
0.8529	High Similarity	NPC138908
0.8515	High Similarity	NPC470310
0.8515	High Similarity	NPC87927
0.8511	High Similarity	NPC471900
0.8511	High Similarity	NPC16377
0.85	High Similarity	NPC39683
0.85	High Similarity	NPC471790
0.85	High Similarity	NPC236585
0.8495	Intermediate Similarity	NPC70661
0.8485	Intermediate Similarity	NPC16911
0.8485	Intermediate Similarity	NPC89099
0.8485	Intermediate Similarity	NPC78427
0.8485	Intermediate Similarity	NPC119036
0.8469	Intermediate Similarity	NPC327788
0.8469	Intermediate Similarity	NPC200054
0.8469	Intermediate Similarity	NPC29410
0.8447	Intermediate Similarity	NPC201908
0.8447	Intermediate Similarity	NPC176949
0.8447	Intermediate Similarity	NPC166993
0.8438	Intermediate Similarity	NPC471901
0.8438	Intermediate Similarity	NPC475416
0.8438	Intermediate Similarity	NPC470230
0.8431	Intermediate Similarity	NPC98603
0.8431	Intermediate Similarity	NPC84928
0.8421	Intermediate Similarity	NPC24705
0.8421	Intermediate Similarity	NPC56962
0.8404	Intermediate Similarity	NPC269360
0.8404	Intermediate Similarity	NPC134197
0.8404	Intermediate Similarity	NPC33768
0.8404	Intermediate Similarity	NPC264005
0.84	Intermediate Similarity	NPC470388
0.8396	Intermediate Similarity	NPC476964
0.8384	Intermediate Similarity	NPC170978
0.8384	Intermediate Similarity	NPC10864
0.8367	Intermediate Similarity	NPC98639
0.8367	Intermediate Similarity	NPC205173
0.8365	Intermediate Similarity	NPC218123
0.8365	Intermediate Similarity	NPC211224
0.8365	Intermediate Similarity	NPC112895
0.8365	Intermediate Similarity	NPC273155
0.8365	Intermediate Similarity	NPC231278
0.8351	Intermediate Similarity	NPC477855
0.8351	Intermediate Similarity	NPC294263
0.835	Intermediate Similarity	NPC265127
0.835	Intermediate Similarity	NPC28791
0.835	Intermediate Similarity	NPC285927
0.8333	Intermediate Similarity	NPC194485
0.8333	Intermediate Similarity	NPC53890
0.8333	Intermediate Similarity	NPC209298
0.8333	Intermediate Similarity	NPC219937
0.8333	Intermediate Similarity	NPC123252
0.8333	Intermediate Similarity	NPC169933
0.8333	Intermediate Similarity	NPC139347
0.8333	Intermediate Similarity	NPC122811
0.8333	Intermediate Similarity	NPC277074
0.8333	Intermediate Similarity	NPC216114
0.8333	Intermediate Similarity	NPC10274
0.8302	Intermediate Similarity	NPC470281
0.8302	Intermediate Similarity	NPC470311
0.8302	Intermediate Similarity	NPC94650
0.8298	Intermediate Similarity	NPC12774
0.8298	Intermediate Similarity	NPC2783
0.8283	Intermediate Similarity	NPC13949
0.828	Intermediate Similarity	NPC299963
0.8269	Intermediate Similarity	NPC251824
0.8269	Intermediate Similarity	NPC471246
0.8269	Intermediate Similarity	NPC86852
0.8265	Intermediate Similarity	NPC215271
0.8265	Intermediate Similarity	NPC153775
0.8265	Intermediate Similarity	NPC29247
0.8265	Intermediate Similarity	NPC289539
0.8265	Intermediate Similarity	NPC261333
0.8265	Intermediate Similarity	NPC111524
0.8265	Intermediate Similarity	NPC104371
0.8265	Intermediate Similarity	NPC91772
0.8265	Intermediate Similarity	NPC101233
0.8265	Intermediate Similarity	NPC292374
0.8265	Intermediate Similarity	NPC129004
0.8265	Intermediate Similarity	NPC277399
0.8252	Intermediate Similarity	NPC301787
0.8247	Intermediate Similarity	NPC198054
0.8247	Intermediate Similarity	NPC250753
0.8229	Intermediate Similarity	NPC471043
0.8218	Intermediate Similarity	NPC477521
0.8211	Intermediate Similarity	NPC4643
0.8211	Intermediate Similarity	NPC259009
0.8211	Intermediate Similarity	NPC57469
0.8208	Intermediate Similarity	NPC255655
0.8208	Intermediate Similarity	NPC130302
0.8191	Intermediate Similarity	NPC264317
0.8191	Intermediate Similarity	NPC294438
0.8182	Intermediate Similarity	NPC279974
0.8182	Intermediate Similarity	NPC210214
0.8173	Intermediate Similarity	NPC222833
0.8173	Intermediate Similarity	NPC4115
0.8172	Intermediate Similarity	NPC471037
0.8165	Intermediate Similarity	NPC469794
0.8165	Intermediate Similarity	NPC72772
0.8163	Intermediate Similarity	NPC199543
0.8163	Intermediate Similarity	NPC26046
0.8163	Intermediate Similarity	NPC181594
0.8163	Intermediate Similarity	NPC291373
0.8163	Intermediate Similarity	NPC144739
0.8155	Intermediate Similarity	NPC96217
0.8155	Intermediate Similarity	NPC222153
0.8144	Intermediate Similarity	NPC46758
0.8144	Intermediate Similarity	NPC80401
0.8144	Intermediate Similarity	NPC100313
0.8137	Intermediate Similarity	NPC148279
0.8137	Intermediate Similarity	NPC289670
0.8137	Intermediate Similarity	NPC252614
0.8125	Intermediate Similarity	NPC160304
0.8125	Intermediate Similarity	NPC474719
0.8125	Intermediate Similarity	NPC183374
0.8125	Intermediate Similarity	NPC4309
0.8125	Intermediate Similarity	NPC211162
0.8113	Intermediate Similarity	NPC154906
0.8113	Intermediate Similarity	NPC471250
0.8105	Intermediate Similarity	NPC475007
0.81	Intermediate Similarity	NPC195366
0.81	Intermediate Similarity	NPC114743
0.81	Intermediate Similarity	NPC135548
0.81	Intermediate Similarity	NPC264979

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 NPC180733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	2130
0.2-0.3	4012
0.3-0.4	1840
0.4-0.5	482
0.5-0.6	226
0.6-0.7	204
0.7-0.8	47
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
0.8191	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD8035	Phase 2
0.7879	Intermediate Similarity	NPD8034	Phase 2
0.7864	Intermediate Similarity	NPD7639	Approved
0.7864	Intermediate Similarity	NPD7640	Approved
0.7826	Intermediate Similarity	NPD6114	Approved
0.7826	Intermediate Similarity	NPD6697	Approved
0.7826	Intermediate Similarity	NPD6118	Approved
0.7826	Intermediate Similarity	NPD6115	Approved
0.7767	Intermediate Similarity	NPD7638	Approved
0.7609	Intermediate Similarity	NPD6117	Approved
0.7527	Intermediate Similarity	NPD6116	Phase 1
0.7523	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7391	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7632	Discontinued
0.7364	Intermediate Similarity	NPD7320	Approved
0.7364	Intermediate Similarity	NPD6899	Approved
0.7364	Intermediate Similarity	NPD6881	Approved
0.7355	Intermediate Similarity	NPD7319	Approved
0.7353	Intermediate Similarity	NPD7637	Suspended
0.7353	Intermediate Similarity	NPD6079	Approved
0.7312	Intermediate Similarity	NPD3703	Phase 2
0.7304	Intermediate Similarity	NPD7115	Discovery
0.7297	Intermediate Similarity	NPD6372	Approved
0.7297	Intermediate Similarity	NPD6373	Approved
0.7282	Intermediate Similarity	NPD6399	Phase 3
0.7273	Intermediate Similarity	NPD5701	Approved
0.7273	Intermediate Similarity	NPD5697	Approved
0.7265	Intermediate Similarity	NPD6319	Approved
0.7232	Intermediate Similarity	NPD7102	Approved
0.7232	Intermediate Similarity	NPD6883	Approved
0.7232	Intermediate Similarity	NPD7290	Approved
0.7222	Intermediate Similarity	NPD5211	Phase 2
0.7193	Intermediate Similarity	NPD4632	Approved
0.7193	Intermediate Similarity	NPD8133	Approved
0.7184	Intermediate Similarity	NPD7515	Phase 2
0.7182	Intermediate Similarity	NPD6008	Approved
0.7172	Intermediate Similarity	NPD4786	Approved
0.717	Intermediate Similarity	NPD4755	Approved
0.7168	Intermediate Similarity	NPD6847	Approved
0.7168	Intermediate Similarity	NPD6649	Approved
0.7168	Intermediate Similarity	NPD6650	Approved
0.7168	Intermediate Similarity	NPD6617	Approved
0.7168	Intermediate Similarity	NPD8130	Phase 1
0.7168	Intermediate Similarity	NPD6869	Approved
0.7167	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7131	Intermediate Similarity	NPD7736	Approved
0.7119	Intermediate Similarity	NPD6059	Approved
0.7119	Intermediate Similarity	NPD6054	Approved
0.7115	Intermediate Similarity	NPD5779	Approved
0.7115	Intermediate Similarity	NPD5778	Approved
0.7107	Intermediate Similarity	NPD6616	Approved
0.7107	Intermediate Similarity	NPD7507	Approved
0.7105	Intermediate Similarity	NPD8297	Approved
0.7105	Intermediate Similarity	NPD6882	Approved
0.7091	Intermediate Similarity	NPD5141	Approved
0.7083	Intermediate Similarity	NPD7604	Phase 2
0.708	Intermediate Similarity	NPD4634	Approved
0.7075	Intermediate Similarity	NPD5221	Approved
0.7075	Intermediate Similarity	NPD4697	Phase 3
0.7075	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5222	Approved
0.7071	Intermediate Similarity	NPD4788	Approved
0.7054	Intermediate Similarity	NPD6011	Approved
0.7049	Intermediate Similarity	NPD8293	Discontinued
0.7049	Intermediate Similarity	NPD7078	Approved
0.7048	Intermediate Similarity	NPD7748	Approved
0.7037	Intermediate Similarity	NPD4696	Approved
0.7037	Intermediate Similarity	NPD5285	Approved
0.7037	Intermediate Similarity	NPD4700	Approved
0.7037	Intermediate Similarity	NPD5286	Approved
0.703	Intermediate Similarity	NPD3618	Phase 1
0.7019	Intermediate Similarity	NPD6411	Approved
0.7018	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6009	Approved
0.7009	Intermediate Similarity	NPD6084	Phase 2
0.7009	Intermediate Similarity	NPD6083	Phase 2
0.7009	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD6370	Approved
0.6991	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3667	Approved
0.6939	Remote Similarity	NPD7525	Registered
0.6917	Remote Similarity	NPD6016	Approved
0.6917	Remote Similarity	NPD6015	Approved
0.6909	Remote Similarity	NPD5225	Approved
0.6909	Remote Similarity	NPD4633	Approved
0.6909	Remote Similarity	NPD5224	Approved
0.6909	Remote Similarity	NPD5226	Approved
0.6864	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5988	Approved
0.6852	Remote Similarity	NPD7902	Approved
0.6847	Remote Similarity	NPD5174	Approved
0.6847	Remote Similarity	NPD5175	Approved
0.6827	Remote Similarity	NPD6101	Approved
0.6827	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5223	Approved
0.6803	Remote Similarity	NPD8328	Phase 3
0.6792	Remote Similarity	NPD4202	Approved
0.6789	Remote Similarity	NPD4225	Approved
0.6783	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6868	Approved
0.678	Remote Similarity	NPD6274	Approved
0.6777	Remote Similarity	NPD5983	Phase 2
0.6777	Remote Similarity	NPD6921	Approved
0.6774	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7101	Approved
0.675	Remote Similarity	NPD7100	Approved
0.6733	Remote Similarity	NPD6695	Phase 3
0.6731	Remote Similarity	NPD5737	Approved
0.6731	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6672	Approved
0.6726	Remote Similarity	NPD4767	Approved
0.6726	Remote Similarity	NPD4768	Approved
0.6699	Remote Similarity	NPD7334	Approved
0.6699	Remote Similarity	NPD7521	Approved
0.6699	Remote Similarity	NPD6684	Approved
0.6699	Remote Similarity	NPD6409	Approved
0.6699	Remote Similarity	NPD7146	Approved
0.6699	Remote Similarity	NPD5330	Approved
0.6696	Remote Similarity	NPD4754	Approved
0.6694	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD6929	Approved
0.6639	Remote Similarity	NPD6908	Approved
0.6639	Remote Similarity	NPD6909	Approved
0.6636	Remote Similarity	NPD5696	Approved
0.6632	Remote Similarity	NPD6081	Approved
0.6612	Remote Similarity	NPD7516	Approved
0.6609	Remote Similarity	NPD4730	Approved
0.6609	Remote Similarity	NPD4729	Approved
0.6609	Remote Similarity	NPD6686	Approved
0.6609	Remote Similarity	NPD5128	Approved
0.66	Remote Similarity	NPD6931	Approved
0.66	Remote Similarity	NPD6930	Phase 2
0.6598	Remote Similarity	NPD3702	Approved
0.6587	Remote Similarity	NPD6033	Approved
0.6583	Remote Similarity	NPD6317	Approved
0.6574	Remote Similarity	NPD7900	Approved
0.6574	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6903	Approved
0.6566	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5786	Approved
0.6535	Remote Similarity	NPD6902	Approved
0.6529	Remote Similarity	NPD6314	Approved
0.6529	Remote Similarity	NPD6313	Approved
0.6526	Remote Similarity	NPD4789	Approved
0.6526	Remote Similarity	NPD4245	Approved
0.6526	Remote Similarity	NPD4244	Approved
0.6522	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3668	Phase 3
0.6504	Remote Similarity	NPD8296	Approved
0.6504	Remote Similarity	NPD8378	Approved
0.6504	Remote Similarity	NPD8380	Approved
0.6504	Remote Similarity	NPD8335	Approved
0.6504	Remote Similarity	NPD8379	Approved
0.65	Remote Similarity	NPD7645	Phase 2
0.6496	Remote Similarity	NPD5249	Phase 3
0.6496	Remote Similarity	NPD5247	Approved
0.6496	Remote Similarity	NPD5248	Approved
0.6496	Remote Similarity	NPD5251	Approved
0.6496	Remote Similarity	NPD5250	Approved
0.6491	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5360	Phase 3
0.6489	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7750	Discontinued
0.6476	Remote Similarity	NPD7524	Approved
0.6466	Remote Similarity	NPD5168	Approved
0.6465	Remote Similarity	NPD5776	Phase 2
0.6465	Remote Similarity	NPD6925	Approved
0.6458	Remote Similarity	NPD5777	Approved
0.6452	Remote Similarity	NPD4224	Phase 2
0.6441	Remote Similarity	NPD5216	Approved
0.6441	Remote Similarity	NPD5217	Approved
0.6441	Remote Similarity	NPD5215	Approved
0.6429	Remote Similarity	NPD6942	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