NPASS Compound

Structure

NPC470769 OpenBabel07101718222D 42 45 0 0 1 0 0 0 0 0999 V2000 -8.7078 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1691 0.1229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -4.2072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 -3.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 -5.0733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7078 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 1.0933 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.1097 1.5933 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -5.9393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5032 -1.7614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5738 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 -1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 0.1229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.5933 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 37 1 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 40 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 17 1 0 0 0 0 7 8 2 0 0 0 0 7 18 1 0 0 0 0 8 22 1 0 0 0 0 9 32 2 0 0 0 0 10 17 2 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 24 2 0 0 0 0 12 18 2 0 0 0 0 12 23 1 0 0 0 0 13 19 2 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 14 26 2 0 0 0 0 15 33 1 0 0 0 0 16 27 1 0 0 0 0 16 34 1 0 0 0 0 18 28 1 0 0 0 0 20 21 1 0 0 0 0 20 30 2 0 0 0 0 21 15 1 1 0 0 0 21 29 1 0 0 0 0 22 23 2 0 0 0 0 22 35 1 0 0 0 0 23 37 1 0 0 0 0 24 30 1 0 0 0 0 24 38 1 0 0 0 0 25 31 2 0 0 0 0 25 39 1 0 0 0 0 26 31 1 0 0 0 0 26 40 1 0 0 0 0 27 28 1 0 0 0 0 27 41 1 0 0 0 0 28 36 1 0 0 0 0 29 19 1 6 0 0 0 29 42 1 0 0 0 0 30 42 1 0 0 0 0 31 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.21
Volume:	578.198
LogP:	1.852
LogD:	2.118
LogS:	-4.535
# Rotatable Bonds:	13
TPSA:	153.37
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.173
Synthetic Accessibility Score:	4.258
Fsp3:	0.323
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04
MDCK Permeability:	1.4187847227731254e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.821
Human Intestinal Absorption (HIA):	0.166
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.482
Plasma Protein Binding (PPB):	72.04468536376953%
Volume Distribution (VD):	0.716
Pgp-substrate:	27.11914825439453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.835
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.732
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	6.307
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.399
Maximum Recommended Daily Dose:	0.809
Skin Sensitization:	0.476
Carcinogencity:	0.1
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.058

Download Data

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

Natural Product: NPC470769

Natural Product ID:	NPC470769
*Common Name:**	Buddlenol A
IUPAC Name:	(E)-3-[(2R,3S)-2-[4-[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal
Synonyms:
Standard InCHIKey:	UYNCCRHOWNHDMT-WWZDYYMFSA-N
Standard InCHI:	InChI=1S/C31H34O11/c1-37-23-12-18(7-8-22(23)35)28(36)27(16-34)41-31-25(39-3)13-19(14-26(31)40-4)29-21(15-33)20-10-17(6-5-9-32)11-24(38-2)30(20)42-29/h5-14,21,27-29,33-36H,15-16H2,1-4H3/b6-5+/t21-,27?,28?,29+/m1/s1
SMILES:	O=C/C=C/c1cc2[C@@H](CO)[C@@H](Oc2c(c1)OC)c1cc(OC)c(c(c1)OC)OC(C(c1ccc(c(c1)OC)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL221879
PubChem CID:	44421295
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792422]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17343407]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	56.9	%	PMID[568947]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	56.8	%	PMID[568947]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	62.6	%	PMID[568947]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	64.8	%	PMID[568947]
NPT1	Others	Radical scavenging activity		IC50	=	147000.0	nM	PMID[568947]
NPT27	Others	Unspecified		Activity	=	129.0	%	PMID[568948]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15280.0	nM	PMID[568948]

☑ 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 NPC470769 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	407
0.1-0.2	1462
0.2-0.3	3793
0.3-0.4	10013
0.4-0.5	8703
0.5-0.6	3437
0.6-0.7	5880
0.7-0.8	7129
0.8-0.85	1422
0.85-0.9	404
0.9-0.95	43
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC470827
0.9667	High Similarity	NPC470828
0.9655	High Similarity	NPC473408
0.9517	High Similarity	NPC260397
0.9379	High Similarity	NPC93433
0.9379	High Similarity	NPC284881
0.9379	High Similarity	NPC474444
0.9379	High Similarity	NPC264706
0.9342	High Similarity	NPC125495
0.9315	High Similarity	NPC181615
0.9295	High Similarity	NPC43065
0.9252	High Similarity	NPC317053
0.9252	High Similarity	NPC324492
0.9189	High Similarity	NPC327412
0.9189	High Similarity	NPC320970
0.9189	High Similarity	NPC320671
0.9189	High Similarity	NPC328567
0.9172	High Similarity	NPC87725
0.9172	High Similarity	NPC263261
0.9128	High Similarity	NPC102934
0.9128	High Similarity	NPC252402
0.9116	High Similarity	NPC470097
0.9116	High Similarity	NPC114119
0.9116	High Similarity	NPC471415
0.911	High Similarity	NPC193722
0.911	High Similarity	NPC278469
0.9103	High Similarity	NPC291101
0.9103	High Similarity	NPC267291
0.9103	High Similarity	NPC266197
0.9079	High Similarity	NPC115203
0.9054	High Similarity	NPC163898
0.9041	High Similarity	NPC224876
0.9041	High Similarity	NPC83375
0.9038	High Similarity	NPC478267
0.9007	High Similarity	NPC477612
0.9	High Similarity	NPC20757
0.9	High Similarity	NPC227516
0.9	High Similarity	NPC236166
0.8986	High Similarity	NPC45257
0.8986	High Similarity	NPC93323
0.8986	High Similarity	NPC12641
0.8986	High Similarity	NPC280092
0.8986	High Similarity	NPC63879
0.8973	High Similarity	NPC184797
0.8973	High Similarity	NPC309124
0.8966	High Similarity	NPC477938
0.8947	High Similarity	NPC329343
0.8947	High Similarity	NPC321972
0.8947	High Similarity	NPC324517
0.894	High Similarity	NPC211561
0.8919	High Similarity	NPC102044
0.8919	High Similarity	NPC85264
0.8919	High Similarity	NPC47633
0.8912	High Similarity	NPC178054
0.8912	High Similarity	NPC311530
0.891	High Similarity	NPC478269
0.8904	High Similarity	NPC473739
0.8904	High Similarity	NPC22517
0.8904	High Similarity	NPC260741
0.8904	High Similarity	NPC70682
0.8904	High Similarity	NPC232164
0.8904	High Similarity	NPC236306
0.8897	High Similarity	NPC77861
0.8897	High Similarity	NPC263367
0.8897	High Similarity	NPC209985
0.8897	High Similarity	NPC177160
0.8897	High Similarity	NPC10737
0.8897	High Similarity	NPC156502
0.8897	High Similarity	NPC29799
0.8897	High Similarity	NPC477939
0.8897	High Similarity	NPC54743
0.8882	High Similarity	NPC472709
0.8882	High Similarity	NPC472710
0.8867	High Similarity	NPC268515
0.8867	High Similarity	NPC40222
0.8851	High Similarity	NPC67467
0.8851	High Similarity	NPC107161
0.8851	High Similarity	NPC131971
0.8844	High Similarity	NPC160283
0.8844	High Similarity	NPC254759
0.8831	High Similarity	NPC475141
0.8816	High Similarity	NPC470098
0.8816	High Similarity	NPC475250
0.8816	High Similarity	NPC470826
0.8816	High Similarity	NPC473266
0.8808	High Similarity	NPC263940
0.8808	High Similarity	NPC18185
0.8808	High Similarity	NPC262911
0.8808	High Similarity	NPC294558
0.8808	High Similarity	NPC70409
0.8808	High Similarity	NPC108811
0.8808	High Similarity	NPC21776
0.8808	High Similarity	NPC170103
0.8808	High Similarity	NPC16269
0.8808	High Similarity	NPC236202
0.8808	High Similarity	NPC82917
0.8808	High Similarity	NPC58190
0.8808	High Similarity	NPC202742
0.8808	High Similarity	NPC101376
0.8808	High Similarity	NPC204770
0.8797	High Similarity	NPC469889
0.8792	High Similarity	NPC477616
0.879	High Similarity	NPC230531
0.879	High Similarity	NPC215400
0.8784	High Similarity	NPC471389
0.8784	High Similarity	NPC35216
0.8784	High Similarity	NPC247291
0.8776	High Similarity	NPC292882
0.8774	High Similarity	NPC157333
0.8774	High Similarity	NPC473736
0.8774	High Similarity	NPC268484
0.8767	High Similarity	NPC248727
0.8767	High Similarity	NPC162659
0.8767	High Similarity	NPC306441
0.8767	High Similarity	NPC270456
0.8767	High Similarity	NPC16435
0.8767	High Similarity	NPC470802
0.8767	High Similarity	NPC265433
0.8766	High Similarity	NPC302610
0.8766	High Similarity	NPC476434
0.8765	High Similarity	NPC180768
0.8759	High Similarity	NPC326095
0.8759	High Similarity	NPC476387
0.8759	High Similarity	NPC119060
0.8759	High Similarity	NPC244983
0.8759	High Similarity	NPC287745
0.8759	High Similarity	NPC193026
0.8759	High Similarity	NPC187616
0.8759	High Similarity	NPC249791
0.8759	High Similarity	NPC237594
0.8759	High Similarity	NPC49603
0.875	High Similarity	NPC187398
0.875	High Similarity	NPC270751
0.875	High Similarity	NPC329836
0.875	High Similarity	NPC476348
0.8742	High Similarity	NPC96576
0.8733	High Similarity	NPC50250
0.8733	High Similarity	NPC304894
0.8733	High Similarity	NPC473108
0.8733	High Similarity	NPC15659
0.8725	High Similarity	NPC204347
0.8725	High Similarity	NPC2613
0.8725	High Similarity	NPC59841
0.8725	High Similarity	NPC475891
0.8718	High Similarity	NPC180901
0.8718	High Similarity	NPC300757
0.8716	High Similarity	NPC22317
0.8716	High Similarity	NPC27495
0.8716	High Similarity	NPC259519
0.871	High Similarity	NPC149735
0.871	High Similarity	NPC223720
0.8701	High Similarity	NPC2745
0.8699	High Similarity	NPC112939
0.8699	High Similarity	NPC256262
0.8699	High Similarity	NPC94750
0.8699	High Similarity	NPC214729
0.8699	High Similarity	NPC61946
0.8699	High Similarity	NPC260898
0.8699	High Similarity	NPC93783
0.8699	High Similarity	NPC112246
0.8699	High Similarity	NPC474206
0.8699	High Similarity	NPC234333
0.8699	High Similarity	NPC47398
0.8699	High Similarity	NPC121812
0.8699	High Similarity	NPC473413
0.8699	High Similarity	NPC470356
0.869	High Similarity	NPC475840
0.869	High Similarity	NPC26394
0.869	High Similarity	NPC36490
0.869	High Similarity	NPC158331
0.8684	High Similarity	NPC15956
0.8684	High Similarity	NPC224674
0.8684	High Similarity	NPC476347
0.8684	High Similarity	NPC114505
0.8684	High Similarity	NPC193473
0.8684	High Similarity	NPC275284
0.8684	High Similarity	NPC213074
0.8684	High Similarity	NPC39657
0.8684	High Similarity	NPC31325
0.8675	High Similarity	NPC469557
0.8671	High Similarity	NPC173726
0.8671	High Similarity	NPC241600
0.8667	High Similarity	NPC163508
0.8667	High Similarity	NPC469630
0.8667	High Similarity	NPC173203
0.8667	High Similarity	NPC474104
0.8662	High Similarity	NPC165483
0.8662	High Similarity	NPC228357
0.8658	High Similarity	NPC471414
0.8658	High Similarity	NPC470372
0.8654	High Similarity	NPC8712
0.865	High Similarity	NPC279209
0.865	High Similarity	NPC102277
0.8649	High Similarity	NPC245207
0.8649	High Similarity	NPC6300
0.8649	High Similarity	NPC319647
0.8649	High Similarity	NPC114171
0.8649	High Similarity	NPC25966
0.8649	High Similarity	NPC230124
0.8649	High Similarity	NPC127218

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 NPC470769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	889
0.2-0.3	1739
0.3-0.4	2772
0.4-0.5	1724
0.5-0.6	942
0.6-0.7	600
0.7-0.8	129
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8493	Intermediate Similarity	NPD1613	Approved
0.8493	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD3027	Phase 3
0.8231	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1934	Approved
0.8101	Intermediate Similarity	NPD1653	Approved
0.8098	Intermediate Similarity	NPD6234	Discontinued
0.8095	Intermediate Similarity	NPD4908	Phase 1
0.8084	Intermediate Similarity	NPD3818	Discontinued
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD7199	Phase 2
0.7976	Intermediate Similarity	NPD7228	Approved
0.7975	Intermediate Similarity	NPD4965	Approved
0.7975	Intermediate Similarity	NPD3882	Suspended
0.7975	Intermediate Similarity	NPD4967	Phase 2
0.7975	Intermediate Similarity	NPD4966	Approved
0.7939	Intermediate Similarity	NPD5494	Approved
0.7882	Intermediate Similarity	NPD7074	Phase 3
0.7853	Intermediate Similarity	NPD2801	Approved
0.7824	Intermediate Similarity	NPD7054	Approved
0.7811	Intermediate Similarity	NPD7473	Discontinued
0.7805	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD4380	Phase 2
0.774	Intermediate Similarity	NPD1610	Phase 2
0.7738	Intermediate Similarity	NPD6232	Discontinued
0.7733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7075	Discontinued
0.7707	Intermediate Similarity	NPD6674	Discontinued
0.7692	Intermediate Similarity	NPD7266	Discontinued
0.7667	Intermediate Similarity	NPD2861	Phase 2
0.7647	Intermediate Similarity	NPD4060	Phase 1
0.7632	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1511	Approved
0.7614	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5124	Phase 1
0.759	Intermediate Similarity	NPD3817	Phase 2
0.7586	Intermediate Similarity	NPD7251	Discontinued
0.7574	Intermediate Similarity	NPD8127	Discontinued
0.7566	Intermediate Similarity	NPD4625	Phase 3
0.7545	Intermediate Similarity	NPD7768	Phase 2
0.7543	Intermediate Similarity	NPD7549	Discontinued
0.7543	Intermediate Similarity	NPD7808	Phase 3
0.7532	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3620	Phase 2
0.7531	Intermediate Similarity	NPD1512	Approved
0.753	Intermediate Similarity	NPD7819	Suspended
0.753	Intermediate Similarity	NPD1465	Phase 2
0.753	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7517	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7240	Approved
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6959	Discontinued
0.747	Intermediate Similarity	NPD6801	Discontinued
0.7469	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3018	Phase 2
0.7427	Intermediate Similarity	NPD7229	Phase 3
0.7414	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7411	Suspended
0.7407	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4749	Approved
0.7391	Intermediate Similarity	NPD6190	Approved
0.7375	Intermediate Similarity	NPD1652	Phase 2
0.7368	Intermediate Similarity	NPD1247	Approved
0.7358	Intermediate Similarity	NPD5763	Approved
0.7358	Intermediate Similarity	NPD5762	Approved
0.7353	Intermediate Similarity	NPD919	Approved
0.7351	Intermediate Similarity	NPD8651	Approved
0.7321	Intermediate Similarity	NPD8455	Phase 2
0.7312	Intermediate Similarity	NPD1549	Phase 2
0.7312	Intermediate Similarity	NPD2424	Discontinued
0.7293	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2983	Phase 2
0.7285	Intermediate Similarity	NPD2982	Phase 2
0.7283	Intermediate Similarity	NPD3926	Phase 2
0.7278	Intermediate Similarity	NPD5402	Approved
0.7278	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7261	Intermediate Similarity	NPD6355	Discontinued
0.7261	Intermediate Similarity	NPD5735	Approved
0.7256	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5283	Phase 1
0.7233	Intermediate Similarity	NPD5588	Approved
0.7222	Intermediate Similarity	NPD3750	Approved
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.7219	Intermediate Similarity	NPD2981	Phase 2
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.7202	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7680	Approved
0.7195	Intermediate Similarity	NPD4357	Discontinued
0.7193	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7685	Pre-registration
0.7188	Intermediate Similarity	NPD6099	Approved
0.7188	Intermediate Similarity	NPD6100	Approved
0.7188	Intermediate Similarity	NPD2796	Approved
0.7186	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD6798	Discontinued
0.717	Intermediate Similarity	NPD4538	Approved
0.717	Intermediate Similarity	NPD4536	Approved
0.717	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5403	Approved
0.7167	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD7906	Approved
0.7143	Intermediate Similarity	NPD7157	Approved
0.7134	Intermediate Similarity	NPD5058	Phase 3
0.7125	Intermediate Similarity	NPD1510	Phase 2
0.7117	Intermediate Similarity	NPD7466	Approved
0.7117	Intermediate Similarity	NPD6331	Phase 2
0.7115	Intermediate Similarity	NPD7095	Approved
0.7108	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD228	Approved
0.7091	Intermediate Similarity	NPD6799	Approved
0.7091	Intermediate Similarity	NPD7212	Phase 2
0.7091	Intermediate Similarity	NPD7213	Phase 3
0.7089	Intermediate Similarity	NPD4140	Approved
0.7088	Intermediate Similarity	NPD4663	Approved
0.7081	Intermediate Similarity	NPD1551	Phase 2
0.7081	Intermediate Similarity	NPD2935	Discontinued
0.7072	Intermediate Similarity	NPD8053	Approved
0.7072	Intermediate Similarity	NPD8054	Approved
0.7063	Intermediate Similarity	NPD7097	Phase 1
0.7062	Intermediate Similarity	NPD3751	Discontinued
0.7059	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7843	Approved
0.7049	Intermediate Similarity	NPD6843	Phase 3
0.7049	Intermediate Similarity	NPD6841	Approved
0.7049	Intermediate Similarity	NPD6842	Approved
0.7048	Intermediate Similarity	NPD2534	Approved
0.7048	Intermediate Similarity	NPD5401	Approved
0.7048	Intermediate Similarity	NPD2532	Approved
0.7048	Intermediate Similarity	NPD2533	Approved
0.7047	Intermediate Similarity	NPD5536	Phase 2
0.7045	Intermediate Similarity	NPD27	Approved
0.7045	Intermediate Similarity	NPD2489	Approved
0.7044	Intermediate Similarity	NPD230	Phase 1
0.7041	Intermediate Similarity	NPD6599	Discontinued
0.7039	Intermediate Similarity	NPD3705	Approved
0.7039	Intermediate Similarity	NPD1091	Approved
0.7037	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6002	Phase 3
0.7037	Intermediate Similarity	NPD6004	Phase 3
0.7037	Intermediate Similarity	NPD6005	Phase 3
0.7037	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3051	Approved
0.7025	Intermediate Similarity	NPD6233	Phase 2
0.7019	Intermediate Similarity	NPD5960	Phase 3
0.7017	Intermediate Similarity	NPD7312	Approved
0.7017	Intermediate Similarity	NPD4577	Approved
0.7017	Intermediate Similarity	NPD7313	Approved
0.7017	Intermediate Similarity	NPD7310	Approved
0.7017	Intermediate Similarity	NPD4578	Approved
0.7017	Intermediate Similarity	NPD7311	Approved
0.7013	Intermediate Similarity	NPD6696	Suspended
0.7012	Intermediate Similarity	NPD8166	Discontinued
0.7012	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD3892	Phase 2
0.7012	Intermediate Similarity	NPD4110	Phase 3
0.7006	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6653	Approved
0.6994	Remote Similarity	NPD3749	Approved
0.6989	Remote Similarity	NPD2969	Approved
0.6989	Remote Similarity	NPD2970	Approved
0.6987	Remote Similarity	NPD9494	Approved
0.6981	Remote Similarity	NPD1240	Approved
0.6981	Remote Similarity	NPD1558	Phase 1
0.6978	Remote Similarity	NPD7309	Approved
0.697	Remote Similarity	NPD7047	Phase 3
0.697	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2797	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