NPASS Compound

Structure

NPC71706 OpenBabel07101719252D 37 41 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 -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 0 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 16 2 0 0 0 0 2 16 1 0 0 0 0 3 26 1 0 0 0 0 6 7 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 29 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 17 6 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 26 1 1 0 0 0 19 31 2 0 0 0 0 20 27 1 6 0 0 0 20 29 1 0 0 0 0 21 28 1 1 0 0 0 21 30 1 0 0 0 0 22 28 1 1 0 0 0 22 32 1 0 0 0 0 23 30 1 6 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 25 28 1 0 0 0 0 25 36 2 0 0 0 0 25 37 1 0 0 0 0 26 27 1 1 0 0 0 27 4 1 6 0 0 0 28 5 1 1 0 0 0 29 30 1 6 0 0 0 30 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.31
Volume:	535.639
LogP:	1.749
LogD:	1.955
LogS:	-4.201
# Rotatable Bonds:	7
TPSA:	132.13
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	6.031
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.105
MDCK Permeability:	5.626859547191998e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.09
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.844

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.651
Plasma Protein Binding (PPB):	82.3329086303711%
Volume Distribution (VD):	0.455
Pgp-substrate:	10.98168659210205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.666
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.37
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.239
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	2.231
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.657
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.179
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.862
Carcinogencity:	0.623
Eye Corrosion:	0.005
Eye Irritation:	0.024
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC71706

Natural Product ID:	NPC71706
*Common Name:**	Quadrangularic Acid H
IUPAC Name:	n.a.
Synonyms:	Quadrangularic Acid H
Standard InCHIKey:	NLELKFNNSPFKBZ-KIOOGCJKSA-N
Standard InCHI:	InChI=1S/C30H44O7/c1-16(2)19(31)7-6-17(24(34)35)18-10-11-27(4)20-8-9-21-28(5,25(36)37)22(32)14-23(33)30(21)15-29(20,30)13-12-26(18,27)3/h17-18,20-23,32-33H,1,6-15H2,2-5H3,(H,34,35)(H,36,37)/t17-,18-,20+,21+,22+,23+,26-,27+,28+,29+,30-/m1/s1
SMILES:	CC(=C)C(=O)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)[C@@H](O)C[C@@H]([C@@]2(C)C(=O)O)O)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515770
PubChem CID:	10768191
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	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	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[478634]

☑ 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 NPC71706 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	237
0.1-0.2	1877
0.2-0.3	6498
0.3-0.4	12559
0.4-0.5	8627
0.5-0.6	6049
0.6-0.7	5070
0.7-0.8	1537
0.8-0.85	141
0.85-0.9	88
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9462	High Similarity	NPC288906
0.9462	High Similarity	NPC266431
0.9462	High Similarity	NPC263135
0.9184	High Similarity	NPC312900
0.9158	High Similarity	NPC234564
0.9158	High Similarity	NPC470387
0.914	High Similarity	NPC198242
0.914	High Similarity	NPC211403
0.9072	High Similarity	NPC41971
0.9072	High Similarity	NPC94906
0.9072	High Similarity	NPC37047
0.9072	High Similarity	NPC180733
0.898	High Similarity	NPC46848
0.8969	High Similarity	NPC472028
0.8958	High Similarity	NPC329910
0.8947	High Similarity	NPC470385
0.8947	High Similarity	NPC470386
0.89	High Similarity	NPC84928
0.89	High Similarity	NPC98603
0.8889	High Similarity	NPC286519
0.8889	High Similarity	NPC246736
0.8889	High Similarity	NPC148628
0.8889	High Similarity	NPC271980
0.8889	High Similarity	NPC124544
0.8889	High Similarity	NPC76866
0.8889	High Similarity	NPC304832
0.8889	High Similarity	NPC214946
0.8889	High Similarity	NPC88203
0.8889	High Similarity	NPC193934
0.8889	High Similarity	NPC275990
0.8854	High Similarity	NPC470232
0.8854	High Similarity	NPC470229
0.8817	High Similarity	NPC146937
0.88	High Similarity	NPC470310
0.88	High Similarity	NPC216114
0.8788	High Similarity	NPC75941
0.8788	High Similarity	NPC289148
0.8788	High Similarity	NPC163963
0.8788	High Similarity	NPC52899
0.8776	High Similarity	NPC20479
0.8776	High Similarity	NPC38296
0.8776	High Similarity	NPC162459
0.8776	High Similarity	NPC471038
0.8776	High Similarity	NPC38471
0.8776	High Similarity	NPC98837
0.8776	High Similarity	NPC28864
0.8776	High Similarity	NPC474793
0.8763	High Similarity	NPC140242
0.875	High Similarity	NPC47853
0.875	High Similarity	NPC153775
0.875	High Similarity	NPC111524
0.875	High Similarity	NPC104371
0.875	High Similarity	NPC475118
0.875	High Similarity	NPC101233
0.875	High Similarity	NPC261333
0.875	High Similarity	NPC129004
0.875	High Similarity	NPC29247
0.875	High Similarity	NPC289539
0.875	High Similarity	NPC91772
0.875	High Similarity	NPC292374
0.875	High Similarity	NPC215271
0.871	High Similarity	NPC259009
0.8687	High Similarity	NPC55503
0.8687	High Similarity	NPC293866
0.8687	High Similarity	NPC287676
0.8687	High Similarity	NPC156324
0.8673	High Similarity	NPC10864
0.866	High Similarity	NPC98639
0.8646	High Similarity	NPC224060
0.8646	High Similarity	NPC244356
0.8646	High Similarity	NPC294263
0.8646	High Similarity	NPC144739
0.8646	High Similarity	NPC181594
0.8641	High Similarity	NPC211224
0.8632	High Similarity	NPC80401
0.8627	High Similarity	NPC138908
0.8627	High Similarity	NPC200957
0.8627	High Similarity	NPC265127
0.8614	High Similarity	NPC87927
0.8602	High Similarity	NPC302111
0.86	High Similarity	NPC471790
0.86	High Similarity	NPC236585
0.8586	High Similarity	NPC78427
0.8586	High Similarity	NPC89099
0.8586	High Similarity	NPC16911
0.8571	High Similarity	NPC264979
0.8571	High Similarity	NPC13949
0.8571	High Similarity	NPC29410
0.8571	High Similarity	NPC200054
0.8571	High Similarity	NPC135548
0.8557	High Similarity	NPC64006
0.8544	High Similarity	NPC201908
0.8544	High Similarity	NPC176949
0.8544	High Similarity	NPC166993
0.8542	High Similarity	NPC470230
0.8542	High Similarity	NPC476168
0.8542	High Similarity	NPC250753
0.8542	High Similarity	NPC299185
0.8529	High Similarity	NPC474558
0.8529	High Similarity	NPC201763
0.8526	High Similarity	NPC57954
0.8526	High Similarity	NPC213832
0.8511	High Similarity	NPC153604
0.85	High Similarity	NPC470388
0.8495	Intermediate Similarity	NPC471034
0.8495	Intermediate Similarity	NPC190704
0.8495	Intermediate Similarity	NPC76518
0.8485	Intermediate Similarity	NPC469810
0.8485	Intermediate Similarity	NPC170978
0.8469	Intermediate Similarity	NPC138245
0.8469	Intermediate Similarity	NPC84018
0.8469	Intermediate Similarity	NPC210214
0.8469	Intermediate Similarity	NPC231060
0.8462	Intermediate Similarity	NPC231278
0.8462	Intermediate Similarity	NPC218123
0.8462	Intermediate Similarity	NPC112895
0.8462	Intermediate Similarity	NPC273155
0.8438	Intermediate Similarity	NPC470378
0.8438	Intermediate Similarity	NPC180849
0.8438	Intermediate Similarity	NPC149761
0.8438	Intermediate Similarity	NPC261994
0.8431	Intermediate Similarity	NPC122811
0.8431	Intermediate Similarity	NPC277074
0.8431	Intermediate Similarity	NPC139347
0.8431	Intermediate Similarity	NPC209298
0.8421	Intermediate Similarity	NPC471900
0.8416	Intermediate Similarity	NPC295276
0.8396	Intermediate Similarity	NPC470281
0.8367	Intermediate Similarity	NPC302008
0.8367	Intermediate Similarity	NPC191094
0.8365	Intermediate Similarity	NPC263729
0.835	Intermediate Similarity	NPC301787
0.8333	Intermediate Similarity	NPC24705
0.8333	Intermediate Similarity	NPC56962
0.8333	Intermediate Similarity	NPC471043
0.8318	Intermediate Similarity	NPC476964
0.8317	Intermediate Similarity	NPC127408
0.8317	Intermediate Similarity	NPC291785
0.8316	Intermediate Similarity	NPC264005
0.8316	Intermediate Similarity	NPC174619
0.8316	Intermediate Similarity	NPC57469
0.8316	Intermediate Similarity	NPC269360
0.83	Intermediate Similarity	NPC111187
0.83	Intermediate Similarity	NPC190080
0.83	Intermediate Similarity	NPC253586
0.8286	Intermediate Similarity	NPC163216
0.828	Intermediate Similarity	NPC471036
0.828	Intermediate Similarity	NPC291320
0.8269	Intermediate Similarity	NPC295366
0.8269	Intermediate Similarity	NPC37600
0.8269	Intermediate Similarity	NPC222833
0.8269	Intermediate Similarity	NPC4115
0.8265	Intermediate Similarity	NPC287118
0.8265	Intermediate Similarity	NPC59170
0.8265	Intermediate Similarity	NPC477855
0.8265	Intermediate Similarity	NPC82138
0.8265	Intermediate Similarity	NPC473690
0.8265	Intermediate Similarity	NPC471902
0.8265	Intermediate Similarity	NPC59350
0.8252	Intermediate Similarity	NPC96217
0.8247	Intermediate Similarity	NPC46758
0.8247	Intermediate Similarity	NPC169933
0.8235	Intermediate Similarity	NPC253886
0.8235	Intermediate Similarity	NPC148279
0.8235	Intermediate Similarity	NPC252614
0.8235	Intermediate Similarity	NPC121218
0.8229	Intermediate Similarity	NPC474719
0.8224	Intermediate Similarity	NPC270586
0.8218	Intermediate Similarity	NPC114274
0.8211	Intermediate Similarity	NPC2783
0.8211	Intermediate Similarity	NPC70661
0.8208	Intermediate Similarity	NPC285298
0.8208	Intermediate Similarity	NPC257082
0.82	Intermediate Similarity	NPC327788
0.8191	Intermediate Similarity	NPC146683
0.819	Intermediate Similarity	NPC61071
0.819	Intermediate Similarity	NPC470952
0.8182	Intermediate Similarity	NPC277399
0.8182	Intermediate Similarity	NPC469982
0.8173	Intermediate Similarity	NPC202793
0.8163	Intermediate Similarity	NPC471901
0.8163	Intermediate Similarity	NPC475416
0.8155	Intermediate Similarity	NPC170615
0.8155	Intermediate Similarity	NPC15396
0.8155	Intermediate Similarity	NPC309388
0.8155	Intermediate Similarity	NPC475803
0.8155	Intermediate Similarity	NPC272472
0.8137	Intermediate Similarity	NPC293890
0.8137	Intermediate Similarity	NPC108371
0.8137	Intermediate Similarity	NPC267921
0.8125	Intermediate Similarity	NPC134197
0.8125	Intermediate Similarity	NPC33768
0.8125	Intermediate Similarity	NPC165895
0.8119	Intermediate Similarity	NPC156546
0.8119	Intermediate Similarity	NPC108078
0.8113	Intermediate Similarity	NPC63841
0.8105	Intermediate Similarity	NPC264317
0.8105	Intermediate Similarity	NPC294438
0.8105	Intermediate Similarity	NPC201655
0.81	Intermediate Similarity	NPC29112

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 NPC71706 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	2301
0.2-0.3	4094
0.3-0.4	1682
0.4-0.5	431
0.5-0.6	174
0.6-0.7	164
0.7-0.8	76
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
0.8105	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6079	Approved
0.7778	Intermediate Similarity	NPD5328	Approved
0.7742	Intermediate Similarity	NPD6115	Approved
0.7742	Intermediate Similarity	NPD6697	Approved
0.7742	Intermediate Similarity	NPD6114	Approved
0.7742	Intermediate Similarity	NPD6118	Approved
0.7624	Intermediate Similarity	NPD8034	Phase 2
0.7624	Intermediate Similarity	NPD8035	Phase 2
0.7615	Intermediate Similarity	NPD6881	Approved
0.7615	Intermediate Similarity	NPD6899	Approved
0.7593	Intermediate Similarity	NPD5739	Approved
0.7593	Intermediate Similarity	NPD6675	Approved
0.7593	Intermediate Similarity	NPD7128	Approved
0.7593	Intermediate Similarity	NPD6402	Approved
0.7527	Intermediate Similarity	NPD6117	Approved
0.7526	Intermediate Similarity	NPD4788	Approved
0.7523	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5221	Approved
0.7477	Intermediate Similarity	NPD6883	Approved
0.7477	Intermediate Similarity	NPD7290	Approved
0.7477	Intermediate Similarity	NPD4634	Approved
0.7477	Intermediate Similarity	NPD7102	Approved
0.7455	Intermediate Similarity	NPD7320	Approved
0.7453	Intermediate Similarity	NPD5285	Approved
0.7453	Intermediate Similarity	NPD5286	Approved
0.7453	Intermediate Similarity	NPD4696	Approved
0.7451	Intermediate Similarity	NPD7515	Phase 2
0.7447	Intermediate Similarity	NPD6116	Phase 1
0.7429	Intermediate Similarity	NPD5173	Approved
0.7429	Intermediate Similarity	NPD4755	Approved
0.7419	Intermediate Similarity	NPD3703	Phase 2
0.7411	Intermediate Similarity	NPD8130	Phase 1
0.7411	Intermediate Similarity	NPD6617	Approved
0.7411	Intermediate Similarity	NPD6650	Approved
0.7411	Intermediate Similarity	NPD6869	Approved
0.7411	Intermediate Similarity	NPD6649	Approved
0.7411	Intermediate Similarity	NPD6847	Approved
0.7387	Intermediate Similarity	NPD6373	Approved
0.7387	Intermediate Similarity	NPD6013	Approved
0.7387	Intermediate Similarity	NPD6012	Approved
0.7387	Intermediate Similarity	NPD6372	Approved
0.7387	Intermediate Similarity	NPD6014	Approved
0.7364	Intermediate Similarity	NPD5701	Approved
0.7358	Intermediate Similarity	NPD7638	Approved
0.735	Intermediate Similarity	NPD6319	Approved
0.7345	Intermediate Similarity	NPD6882	Approved
0.7345	Intermediate Similarity	NPD8297	Approved
0.7333	Intermediate Similarity	NPD4697	Phase 3
0.7315	Intermediate Similarity	NPD5226	Approved
0.7315	Intermediate Similarity	NPD4633	Approved
0.7315	Intermediate Similarity	NPD5225	Approved
0.7315	Intermediate Similarity	NPD5224	Approved
0.7315	Intermediate Similarity	NPD5211	Phase 2
0.7312	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD3618	Phase 1
0.7297	Intermediate Similarity	NPD6011	Approved
0.729	Intermediate Similarity	NPD7640	Approved
0.729	Intermediate Similarity	NPD4700	Approved
0.729	Intermediate Similarity	NPD7639	Approved
0.7281	Intermediate Similarity	NPD4632	Approved
0.7273	Intermediate Similarity	NPD4786	Approved
0.725	Intermediate Similarity	NPD7492	Approved
0.7248	Intermediate Similarity	NPD5175	Approved
0.7248	Intermediate Similarity	NPD5174	Approved
0.7241	Intermediate Similarity	NPD7115	Discovery
0.7222	Intermediate Similarity	NPD5223	Approved
0.7213	Intermediate Similarity	NPD7736	Approved
0.7212	Intermediate Similarity	NPD6399	Phase 3
0.7203	Intermediate Similarity	NPD6054	Approved
0.719	Intermediate Similarity	NPD6616	Approved
0.7182	Intermediate Similarity	NPD5141	Approved
0.7167	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7748	Approved
0.7131	Intermediate Similarity	NPD7078	Approved
0.7117	Intermediate Similarity	NPD6008	Approved
0.7105	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6084	Phase 2
0.7103	Intermediate Similarity	NPD6083	Phase 2
0.7097	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6081	Approved
0.7097	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6009	Approved
0.7083	Intermediate Similarity	NPD6370	Approved
0.7075	Intermediate Similarity	NPD4629	Approved
0.7075	Intermediate Similarity	NPD5210	Approved
0.7071	Intermediate Similarity	NPD3667	Approved
0.7059	Intermediate Similarity	NPD6059	Approved
0.7048	Intermediate Similarity	NPD4202	Approved
0.7037	Intermediate Similarity	NPD5696	Approved
0.7016	Intermediate Similarity	NPD7319	Approved
0.7009	Intermediate Similarity	NPD6868	Approved
0.7009	Intermediate Similarity	NPD6274	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.7	Intermediate Similarity	NPD6015	Approved
0.6992	Remote Similarity	NPD8293	Discontinued
0.6991	Remote Similarity	NPD4730	Approved
0.6991	Remote Similarity	NPD4729	Approved
0.6991	Remote Similarity	NPD5128	Approved
0.6975	Remote Similarity	NPD7100	Approved
0.6975	Remote Similarity	NPD7101	Approved
0.6964	Remote Similarity	NPD4768	Approved
0.6964	Remote Similarity	NPD4767	Approved
0.6961	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7902	Approved
0.6942	Remote Similarity	NPD5988	Approved
0.6937	Remote Similarity	NPD4754	Approved
0.6931	Remote Similarity	NPD3133	Approved
0.6931	Remote Similarity	NPD3666	Approved
0.6931	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD4753	Phase 2
0.6916	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6335	Approved
0.6882	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5250	Approved
0.687	Remote Similarity	NPD5251	Approved
0.687	Remote Similarity	NPD5248	Approved
0.687	Remote Similarity	NPD5249	Phase 3
0.687	Remote Similarity	NPD5247	Approved
0.6869	Remote Similarity	NPD7525	Registered
0.686	Remote Similarity	NPD5983	Phase 2
0.6847	Remote Similarity	NPD7632	Discontinued
0.6842	Remote Similarity	NPD5168	Approved
0.6827	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5737	Approved
0.6827	Remote Similarity	NPD6672	Approved
0.681	Remote Similarity	NPD5217	Approved
0.681	Remote Similarity	NPD5215	Approved
0.681	Remote Similarity	NPD5216	Approved
0.6807	Remote Similarity	NPD6317	Approved
0.6796	Remote Similarity	NPD7334	Approved
0.6796	Remote Similarity	NPD7146	Approved
0.6796	Remote Similarity	NPD5330	Approved
0.6796	Remote Similarity	NPD7521	Approved
0.6796	Remote Similarity	NPD6684	Approved
0.6796	Remote Similarity	NPD6409	Approved
0.6792	Remote Similarity	NPD6411	Approved
0.6792	Remote Similarity	NPD7637	Suspended
0.6774	Remote Similarity	NPD7507	Approved
0.6774	Remote Similarity	NPD6336	Discontinued
0.6759	Remote Similarity	NPD5695	Phase 3
0.675	Remote Similarity	NPD6313	Approved
0.675	Remote Similarity	NPD6314	Approved
0.6748	Remote Similarity	NPD8328	Phase 3
0.6724	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5135	Approved
0.6724	Remote Similarity	NPD5169	Approved
0.6721	Remote Similarity	NPD6909	Approved
0.6721	Remote Similarity	NPD6908	Approved
0.6695	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6638	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5279	Phase 3
0.6632	Remote Similarity	NPD4245	Approved
0.6632	Remote Similarity	NPD4789	Approved
0.6632	Remote Similarity	NPD4244	Approved
0.6609	Remote Similarity	NPD6412	Phase 2
0.6604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6101	Approved
0.6602	Remote Similarity	NPD3668	Phase 3
0.6596	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5360	Phase 3
0.6585	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4225	Approved
0.6574	Remote Similarity	NPD5779	Approved
0.6574	Remote Similarity	NPD5778	Approved
0.6571	Remote Similarity	NPD3573	Approved
0.6569	Remote Similarity	NPD4223	Phase 3
0.6569	Remote Similarity	NPD4221	Approved
0.6559	Remote Similarity	NPD4224	Phase 2
0.6545	Remote Similarity	NPD7614	Phase 1
0.6538	Remote Similarity	NPD5329	Approved
0.6535	Remote Similarity	NPD6033	Approved
0.6529	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3698	Phase 2
0.6514	Remote Similarity	NPD6001	Approved
0.65	Remote Similarity	NPD5167	Approved
0.6481	Remote Similarity	NPD5281	Approved
0.6481	Remote Similarity	NPD5284	Approved
0.6452	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6921	Approved
0.6449	Remote Similarity	NPD6673	Approved
0.6449	Remote Similarity	NPD6080	Approved
0.6449	Remote Similarity	NPD6904	Approved
0.6442	Remote Similarity	NPD4197	Approved
0.6441	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6686	Approved
0.6392	Remote Similarity	NPD5777	Approved
0.6373	Remote Similarity	NPD5368	Approved
0.6372	Remote Similarity	NPD8418	Phase 2
0.6364	Remote Similarity	NPD7339	Approved
0.6364	Remote Similarity	NPD6942	Approved
0.6364	Remote Similarity	NPD3702	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