NPASS Compound

Structure

NPC259707 OpenBabel07101718282D 51 58 0 0 1 0 0 0 0 0999 V2000 -1.6723 -4.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3445 -4.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1235 0.5846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4041 -1.0640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -5.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3445 -5.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0753 0.7466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -0.9020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8310 -1.3284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1048 -0.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3445 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5252 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5084 -4.3447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7879 -0.3207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5084 -6.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6915 0.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7754 -0.5863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5084 -1.4482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5084 -0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2161 -1.7477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4899 -0.6826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8361 -0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3445 -2.8964 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6890 -2.8964 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5456 -1.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8361 -1.4482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6890 -1.9310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8529 -1.4482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0168 -1.9310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5084 -3.3792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6723 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8361 -1.4482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0168 -2.8964 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8361 -0.4827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3613 -2.8964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5084 -7.2411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6433 0.1653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3708 0.5015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3445 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3604 -3.6732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5252 -1.4482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8529 -0.4827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1807 -1.4482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 -1.9310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1807 -3.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8529 -3.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -2.8964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1250 -0.2634 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 1 5 1 0 0 0 0 1 14 2 0 0 0 0 2 6 2 0 0 0 0 2 14 1 0 0 0 0 3 7 1 0 0 0 0 3 15 2 0 0 0 0 4 8 2 0 0 0 0 4 15 1 0 0 0 0 5 16 2 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 9 21 1 0 0 0 0 10 18 1 0 0 0 0 10 22 2 0 0 0 0 11 19 1 0 0 0 0 11 24 1 0 0 0 0 12 20 2 0 0 0 0 12 23 1 0 0 0 0 13 37 1 0 0 0 0 16 38 1 0 0 0 0 17 39 1 0 0 0 0 18 40 1 0 0 0 0 19 20 1 0 0 0 0 19 33 2 0 0 0 0 20 41 1 0 0 0 0 21 26 2 0 0 0 0 21 42 1 0 0 0 0 22 26 1 0 0 0 0 22 50 1 0 0 0 0 23 27 2 0 0 0 0 23 51 1 0 0 0 0 24 32 1 0 0 0 0 24 47 1 6 0 0 0 25 13 1 6 0 0 0 25 29 1 0 0 0 0 25 48 1 0 0 0 0 27 28 1 0 0 0 0 27 33 1 0 0 0 0 28 26 1 1 0 0 0 28 34 1 0 0 0 0 29 30 1 0 0 0 0 29 43 1 1 0 0 0 30 31 1 0 0 0 0 30 44 1 6 0 0 0 31 35 1 0 0 0 0 31 45 1 1 0 0 0 32 14 1 1 0 0 0 32 49 1 0 0 0 0 33 49 1 0 0 0 0 34 36 1 1 0 0 0 34 46 1 0 0 0 0 35 47 1 6 0 0 0 35 48 1 0 0 0 0 36 15 1 1 0 0 0 36 50 1 0 0 0 0 36 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	706.19
Volume:	662.976
LogP:	1.686
LogD:	1.251
LogS:	-3.21
# Rotatable Bonds:	5
TPSA:	248.45
# H-Bond Aceptor:	15
# H-Bond Donor:	10
# Rings:	8
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	5.9
Fsp3:	0.333
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.628
MDCK Permeability:	4.217543846607441e-06
Pgp-inhibitor:	0.043
Pgp-substrate:	0.639
Human Intestinal Absorption (HIA):	0.978
20% Bioavailability (F20%):	0.811
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	91.35648345947266%
Volume Distribution (VD):	0.169
Pgp-substrate:	7.27942419052124%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.284
CYP3A4-substrate:	0.419

ADMET: Excretion

Clearance (CL):	6.15
Half-life (T1/2):	0.406

ADMET: Toxicity

hERG Blockers:	0.122
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.383
Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.92
Carcinogencity:	0.652
Eye Corrosion:	0.003
Eye Irritation:	0.827
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC259707

Natural Product ID:	NPC259707
*Common Name:**	OBQUSXFDJKPXLW-SJQIHRIZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OBQUSXFDJKPXLW-SJQIHRIZSA-N
Standard InCHI:	InChI=1S/C36H34O15/c37-13-25-29(43)30(44)31(45)35(48-25)47-24-11-19-20(41)12-23-27(33(19)49-32(24)14-1-5-16(38)6-2-14)28-26-21(42)9-18(40)10-22(26)50-36(51-23,34(28)46)15-3-7-17(39)8-4-15/h1-10,12,24-25,28-32,34-35,37-46H,11,13H2/t24-,25-,28+,29-,30+,31-,32+,34+,35-,36-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2Cc3c(O)cc4c(c3O[C@H]2c2ccc(cc2)O)[C@@H]2c3c(O)cc(cc3O[C@](O4)([C@H]2O)c2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431899
PubChem CID:	72703041
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO32897	spenceria ramalana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24131240]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	32100.0	nM	PMID[545247]

☑ 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 NPC259707 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	504
0.1-0.2	1707
0.2-0.3	4379
0.3-0.4	10632
0.4-0.5	7922
0.5-0.6	5385
0.6-0.7	7504
0.7-0.8	4128
0.8-0.85	395
0.85-0.9	102
0.9-0.95	35
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9724	High Similarity	NPC471403
0.965	High Similarity	NPC248053
0.965	High Similarity	NPC155564
0.965	High Similarity	NPC102280
0.9533	High Similarity	NPC185231
0.9524	High Similarity	NPC59692
0.9338	High Similarity	NPC4809
0.9338	High Similarity	NPC147743
0.9338	High Similarity	NPC73517
0.9301	High Similarity	NPC100482
0.9301	High Similarity	NPC277331
0.9276	High Similarity	NPC106601
0.9276	High Similarity	NPC159526
0.9276	High Similarity	NPC151474
0.9276	High Similarity	NPC86630
0.9276	High Similarity	NPC212614
0.9276	High Similarity	NPC471404
0.9276	High Similarity	NPC205613
0.9262	High Similarity	NPC134911
0.9262	High Similarity	NPC272552
0.9262	High Similarity	NPC322899
0.9262	High Similarity	NPC469944
0.9262	High Similarity	NPC226108
0.9262	High Similarity	NPC46283
0.9262	High Similarity	NPC233467
0.9262	High Similarity	NPC44192
0.9241	High Similarity	NPC225445
0.9241	High Similarity	NPC475492
0.9172	High Similarity	NPC116922
0.911	High Similarity	NPC177597
0.9073	High Similarity	NPC224161
0.9073	High Similarity	NPC20050
0.9073	High Similarity	NPC306267
0.9013	High Similarity	NPC46335
0.9007	High Similarity	NPC226809
0.9007	High Similarity	NPC279406
0.8973	High Similarity	NPC5253
0.8973	High Similarity	NPC472353
0.8973	High Similarity	NPC84207
0.8973	High Similarity	NPC128337
0.8973	High Similarity	NPC139976
0.8973	High Similarity	NPC230718
0.8973	High Similarity	NPC49542
0.8968	High Similarity	NPC100936
0.8968	High Similarity	NPC1253
0.8958	High Similarity	NPC470308
0.8958	High Similarity	NPC262328
0.8958	High Similarity	NPC87777
0.8958	High Similarity	NPC470307
0.894	High Similarity	NPC473621
0.8933	High Similarity	NPC295573
0.8933	High Similarity	NPC470208
0.8926	High Similarity	NPC18185
0.8926	High Similarity	NPC262911
0.8926	High Similarity	NPC294558
0.8926	High Similarity	NPC170103
0.8926	High Similarity	NPC236202
0.8926	High Similarity	NPC82917
0.8926	High Similarity	NPC70409
0.8926	High Similarity	NPC263940
0.8926	High Similarity	NPC58190
0.8926	High Similarity	NPC108811
0.8926	High Similarity	NPC204770
0.8926	High Similarity	NPC202742
0.8904	High Similarity	NPC108674
0.8889	High Similarity	NPC471522
0.8874	High Similarity	NPC477612
0.8867	High Similarity	NPC280945
0.8859	High Similarity	NPC96576
0.8854	High Similarity	NPC12326
0.8819	High Similarity	NPC79957
0.8808	High Similarity	NPC211561
0.88	High Similarity	NPC473480
0.88	High Similarity	NPC15538
0.879	High Similarity	NPC48880
0.8776	High Similarity	NPC257095
0.8776	High Similarity	NPC273932
0.8776	High Similarity	NPC89686
0.8765	High Similarity	NPC168789
0.875	High Similarity	NPC476616
0.875	High Similarity	NPC476617
0.875	High Similarity	NPC476615
0.8742	High Similarity	NPC227516
0.8742	High Similarity	NPC20757
0.8733	High Similarity	NPC74320
0.8733	High Similarity	NPC107120
0.8725	High Similarity	NPC469313
0.8725	High Similarity	NPC76176
0.8725	High Similarity	NPC138227
0.8725	High Similarity	NPC168579
0.8675	High Similarity	NPC153182
0.8675	High Similarity	NPC174251
0.8658	High Similarity	NPC37793
0.8649	High Similarity	NPC210192
0.8649	High Similarity	NPC5155
0.8639	High Similarity	NPC475836
0.863	High Similarity	NPC138350
0.863	High Similarity	NPC165482
0.863	High Similarity	NPC3293
0.863	High Similarity	NPC197723
0.863	High Similarity	NPC40664
0.8627	High Similarity	NPC472709
0.8627	High Similarity	NPC472710
0.8621	High Similarity	NPC188555
0.8621	High Similarity	NPC130496
0.8618	High Similarity	NPC270751
0.8609	High Similarity	NPC215678
0.8609	High Similarity	NPC274454
0.8609	High Similarity	NPC125755
0.86	High Similarity	NPC28440
0.86	High Similarity	NPC171932
0.8563	High Similarity	NPC321916
0.8562	High Similarity	NPC238243
0.8543	High Similarity	NPC475096
0.8543	High Similarity	NPC161700
0.8543	High Similarity	NPC277867
0.8542	High Similarity	NPC103799
0.8523	High Similarity	NPC178054
0.8516	High Similarity	NPC21902
0.8512	High Similarity	NPC318119
0.8506	High Similarity	NPC469707
0.8506	High Similarity	NPC182368
0.8506	High Similarity	NPC225815
0.8506	High Similarity	NPC185955
0.8506	High Similarity	NPC214326
0.8506	High Similarity	NPC9933
0.8506	High Similarity	NPC260781
0.8506	High Similarity	NPC218041
0.8506	High Similarity	NPC145979
0.8506	High Similarity	NPC469706
0.8497	Intermediate Similarity	NPC281549
0.8487	Intermediate Similarity	NPC14468
0.8487	Intermediate Similarity	NPC190714
0.8487	Intermediate Similarity	NPC99515
0.8483	Intermediate Similarity	NPC85799
0.8483	Intermediate Similarity	NPC165686
0.8483	Intermediate Similarity	NPC303422
0.8483	Intermediate Similarity	NPC26080
0.8462	Intermediate Similarity	NPC78809
0.8457	Intermediate Similarity	NPC9309
0.8446	Intermediate Similarity	NPC134260
0.8442	Intermediate Similarity	NPC321657
0.8442	Intermediate Similarity	NPC318373
0.8435	Intermediate Similarity	NPC125579
0.8431	Intermediate Similarity	NPC213074
0.8431	Intermediate Similarity	NPC275284
0.8431	Intermediate Similarity	NPC31325
0.8431	Intermediate Similarity	NPC227902
0.8431	Intermediate Similarity	NPC39657
0.8431	Intermediate Similarity	NPC224674
0.8431	Intermediate Similarity	NPC15956
0.8431	Intermediate Similarity	NPC193473
0.8431	Intermediate Similarity	NPC114505
0.8425	Intermediate Similarity	NPC92805
0.8425	Intermediate Similarity	NPC115022
0.8425	Intermediate Similarity	NPC294166
0.8421	Intermediate Similarity	NPC226722
0.8421	Intermediate Similarity	NPC181615
0.8421	Intermediate Similarity	NPC476301
0.8421	Intermediate Similarity	NPC23807
0.8421	Intermediate Similarity	NPC43508
0.8414	Intermediate Similarity	NPC121376
0.8411	Intermediate Similarity	NPC473044
0.8408	Intermediate Similarity	NPC157333
0.8403	Intermediate Similarity	NPC93962
0.84	Intermediate Similarity	NPC469661
0.8397	Intermediate Similarity	NPC302610
0.8387	Intermediate Similarity	NPC205501
0.8387	Intermediate Similarity	NPC118000
0.8387	Intermediate Similarity	NPC162976
0.8387	Intermediate Similarity	NPC238140
0.8378	Intermediate Similarity	NPC20829
0.8378	Intermediate Similarity	NPC262585
0.8378	Intermediate Similarity	NPC18189
0.8378	Intermediate Similarity	NPC469383
0.8377	Intermediate Similarity	NPC175976
0.8367	Intermediate Similarity	NPC124085
0.8367	Intermediate Similarity	NPC184269
0.8367	Intermediate Similarity	NPC117048
0.8366	Intermediate Similarity	NPC260397
0.8355	Intermediate Similarity	NPC217635
0.8355	Intermediate Similarity	NPC471667
0.8355	Intermediate Similarity	NPC79429
0.8355	Intermediate Similarity	NPC473045
0.8355	Intermediate Similarity	NPC25292
0.8355	Intermediate Similarity	NPC151704
0.8344	Intermediate Similarity	NPC469559
0.8344	Intermediate Similarity	NPC5262
0.8344	Intermediate Similarity	NPC475227
0.8344	Intermediate Similarity	NPC189115
0.8344	Intermediate Similarity	NPC106669
0.8344	Intermediate Similarity	NPC475084
0.8344	Intermediate Similarity	NPC59516
0.8344	Intermediate Similarity	NPC200645
0.8344	Intermediate Similarity	NPC472714
0.8333	Intermediate Similarity	NPC329343
0.8333	Intermediate Similarity	NPC53986
0.8333	Intermediate Similarity	NPC262189
0.8333	Intermediate Similarity	NPC274717
0.8333	Intermediate Similarity	NPC106944

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 NPC259707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	866
0.2-0.3	1875
0.3-0.4	2852
0.4-0.5	1708
0.5-0.6	962
0.6-0.7	421
0.7-0.8	66
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8645	High Similarity	NPD8455	Phase 2
0.8472	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4908	Phase 1
0.8133	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1091	Approved
0.7972	Intermediate Similarity	NPD1610	Phase 2
0.7922	Intermediate Similarity	NPD6674	Discontinued
0.7914	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8312	Approved
0.7895	Intermediate Similarity	NPD8313	Approved
0.787	Intermediate Similarity	NPD7074	Phase 3
0.7857	Intermediate Similarity	NPD7228	Approved
0.7718	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7054	Approved
0.7683	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7472	Approved
0.7651	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1653	Approved
0.763	Intermediate Similarity	NPD7808	Phase 3
0.7597	Intermediate Similarity	NPD7097	Phase 1
0.7572	Intermediate Similarity	NPD7251	Discontinued
0.7572	Intermediate Similarity	NPD6559	Discontinued
0.7569	Intermediate Similarity	NPD1548	Phase 1
0.755	Intermediate Similarity	NPD3027	Phase 3
0.7546	Intermediate Similarity	NPD4380	Phase 2
0.7533	Intermediate Similarity	NPD2861	Phase 2
0.753	Intermediate Similarity	NPD7768	Phase 2
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7240	Approved
0.7468	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5124	Phase 1
0.7456	Intermediate Similarity	NPD7199	Phase 2
0.7456	Intermediate Similarity	NPD6959	Discontinued
0.7455	Intermediate Similarity	NPD37	Approved
0.7453	Intermediate Similarity	NPD7447	Phase 1
0.7452	Intermediate Similarity	NPD7266	Discontinued
0.745	Intermediate Similarity	NPD8651	Approved
0.744	Intermediate Similarity	NPD6234	Discontinued
0.7438	Intermediate Similarity	NPD5058	Phase 3
0.7434	Intermediate Similarity	NPD4625	Phase 3
0.7427	Intermediate Similarity	NPD6166	Phase 2
0.7427	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4965	Approved
0.7425	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4966	Approved
0.7425	Intermediate Similarity	NPD4967	Phase 2
0.7391	Intermediate Similarity	NPD7213	Phase 3
0.7391	Intermediate Similarity	NPD7212	Phase 2
0.7381	Intermediate Similarity	NPD7075	Discontinued
0.7358	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3818	Discontinued
0.731	Intermediate Similarity	NPD3787	Discontinued
0.7293	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7267	Intermediate Similarity	NPD4749	Approved
0.7267	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4538	Approved
0.7261	Intermediate Similarity	NPD4536	Approved
0.7232	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5588	Approved
0.7215	Intermediate Similarity	NPD5960	Phase 3
0.7202	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5844	Phase 1
0.7188	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7783	Phase 2
0.7186	Intermediate Similarity	NPD7411	Suspended
0.7186	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7680	Approved
0.7161	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7843	Approved
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7157	Approved
0.7101	Intermediate Similarity	NPD7819	Suspended
0.7099	Intermediate Similarity	NPD7466	Approved
0.7083	Intermediate Similarity	NPD8151	Discontinued
0.7066	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8054	Approved
0.7056	Intermediate Similarity	NPD8053	Approved
0.7051	Intermediate Similarity	NPD6798	Discontinued
0.7045	Intermediate Similarity	NPD3751	Discontinued
0.7041	Intermediate Similarity	NPD6801	Discontinued
0.7041	Intermediate Similarity	NPD1934	Approved
0.703	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5126	Approved
0.7	Intermediate Similarity	NPD6516	Phase 2
0.7	Intermediate Similarity	NPD5846	Approved
0.7	Intermediate Similarity	NPD5125	Phase 3
0.6995	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1549	Phase 2
0.6964	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5403	Approved
0.6937	Remote Similarity	NPD7119	Phase 2
0.6937	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5735	Approved
0.6914	Remote Similarity	NPD7229	Phase 3
0.6914	Remote Similarity	NPD5762	Approved
0.6914	Remote Similarity	NPD5763	Approved
0.6911	Remote Similarity	NPD7698	Approved
0.6911	Remote Similarity	NPD7696	Phase 3
0.6911	Remote Similarity	NPD7697	Approved
0.6908	Remote Similarity	NPD422	Phase 1
0.6899	Remote Similarity	NPD6233	Phase 2
0.6897	Remote Similarity	NPD5494	Approved
0.6894	Remote Similarity	NPD4108	Discontinued
0.6893	Remote Similarity	NPD7473	Discontinued
0.689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2684	Approved
0.6875	Remote Similarity	NPD7871	Phase 2
0.6875	Remote Similarity	NPD7870	Phase 2
0.6871	Remote Similarity	NPD2424	Discontinued
0.6867	Remote Similarity	NPD7041	Phase 2
0.6867	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5402	Approved
0.6859	Remote Similarity	NPD6823	Phase 2
0.6856	Remote Similarity	NPD7701	Phase 2
0.6852	Remote Similarity	NPD6100	Approved
0.6852	Remote Similarity	NPD6099	Approved
0.6851	Remote Similarity	NPD7549	Discontinued
0.6842	Remote Similarity	NPD6777	Approved
0.6842	Remote Similarity	NPD6779	Approved
0.6842	Remote Similarity	NPD6776	Approved
0.6842	Remote Similarity	NPD6782	Approved
0.6842	Remote Similarity	NPD6780	Approved
0.6842	Remote Similarity	NPD6778	Approved
0.6842	Remote Similarity	NPD6781	Approved
0.6829	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5401	Approved
0.6826	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7435	Discontinued
0.6818	Remote Similarity	NPD6232	Discontinued
0.6818	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8156	Discontinued
0.6807	Remote Similarity	NPD6666	Approved
0.6807	Remote Similarity	NPD6667	Approved
0.6806	Remote Similarity	NPD290	Approved
0.6804	Remote Similarity	NPD7584	Approved
0.6802	Remote Similarity	NPD1465	Phase 2
0.6796	Remote Similarity	NPD7685	Pre-registration
0.6788	Remote Similarity	NPD4628	Phase 3
0.6788	Remote Similarity	NPD8320	Phase 1
0.6788	Remote Similarity	NPD4535	Phase 3
0.6788	Remote Similarity	NPD3892	Phase 2
0.6788	Remote Similarity	NPD8319	Approved
0.6784	Remote Similarity	NPD6072	Discontinued
0.6782	Remote Similarity	NPD3749	Approved
0.6779	Remote Similarity	NPD6671	Approved
0.6772	Remote Similarity	NPD7095	Approved
0.6769	Remote Similarity	NPD7585	Approved
0.6761	Remote Similarity	NPD8127	Discontinued
0.676	Remote Similarity	NPD8252	Approved
0.676	Remote Similarity	NPD8251	Approved
0.676	Remote Similarity	NPD8099	Discontinued
0.6758	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3018	Phase 2
0.6751	Remote Similarity	NPD7801	Approved
0.675	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7699	Phase 2
0.6737	Remote Similarity	NPD7700	Phase 2
0.6726	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7773	Phase 2
0.6718	Remote Similarity	NPD7583	Approved
0.671	Remote Similarity	NPD6582	Phase 2
0.671	Remote Similarity	NPD6583	Phase 3
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2801	Approved
0.6701	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7874	Approved
0.6688	Remote Similarity	NPD6584	Phase 3
0.6688	Remote Similarity	NPD3705	Approved
0.6687	Remote Similarity	NPD1510	Phase 2
0.6687	Remote Similarity	NPD7033	Discontinued
0.6687	Remote Similarity	NPD3748	Approved
0.6684	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD6843	Phase 3

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