NPASS Compound

Structure

CID275278 OpenBabel06191716082D 22 23 0 0 0 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 3.4641 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 9 2 0 0 0 0 3 11 1 0 0 0 0 4 10 2 0 0 0 0 4 12 1 0 0 0 0 5 9 1 0 0 0 0 5 13 2 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 17 2 0 0 0 0 8 10 1 0 0 0 0 8 18 2 0 0 0 0 11 12 1 0 0 0 0 11 15 2 0 0 0 0 12 16 2 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	299.829
LogP:	2.218
LogD:	1.759
LogS:	-4.197
# Rotatable Bonds:	5
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.824
Synthetic Accessibility Score:	2.528
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.881
MDCK Permeability:	8.230699677369557e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.186
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.351

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	93.32019805908203%
Volume Distribution (VD):	0.566
Pgp-substrate:	3.3858065605163574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.517
CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.281
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.224
CYP3A4-inhibitor:	0.183
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	4.752
Half-life (T1/2):	0.845

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.015
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.546
Skin Sensitization:	0.356
Carcinogencity:	0.015
Eye Corrosion:	0.401
Eye Irritation:	0.921
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC275278

Natural Product ID:	NPC275278
*Common Name:**	5,5-Bisvanillin
IUPAC Name:	3-(5-formyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde
Synonyms:	5,5-Bisvanillin
Standard InCHIKey:	NSTQUZVZBUTVPY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-21-13-5-9(7-17)3-11(15(13)19)12-4-10(8-18)6-14(22-2)16(12)20/h3-8,19-20H,1-2H3
SMILES:	COc1cc(C=O)cc(c1O)c1cc(C=O)cc(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL41304
PubChem CID:	95086
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls 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
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11291	Styrax benzoin	Species	Styracaceae	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
GI50	1
IC50	1
Others	8

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
NON-MOLECULAR	5
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3118	Cell Line	Cell line	Homo sapiens	GI50	=	80000.0	nM	PMID[534459]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	86.2	%	PMID[534460]
NPT20788	CELL-LINE	HMEC-1	Homo sapiens	Activity	=	40.5	%	PMID[534460]
NPT35	Others	n.a.		IC50	=	382100.0	nM	PMID[534461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	103.0	%	PMID[534461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	88.0	%	PMID[534461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	19.0	%	PMID[534461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	21.0	%	PMID[534461]
NPT27	Others	Unspecified		Activity	=	100.0	%	PMID[534461]
NPT27	Others	Unspecified		Activity	=	99.0	%	PMID[534461]

☑ 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 NPC275278 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	365
0.1-0.2	1607
0.2-0.3	3995
0.3-0.4	9981
0.4-0.5	8203
0.5-0.6	3161
0.6-0.7	6037
0.7-0.8	7660
0.8-0.85	1448
0.85-0.9	226
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC50954
0.9315	High Similarity	NPC131121
0.9247	High Similarity	NPC75377
0.9189	High Similarity	NPC300757
0.9189	High Similarity	NPC180901
0.8966	High Similarity	NPC287495
0.8966	High Similarity	NPC9370
0.8966	High Similarity	NPC157133
0.8958	High Similarity	NPC46161
0.8958	High Similarity	NPC239608
0.8929	High Similarity	NPC152209
0.8926	High Similarity	NPC137125
0.8926	High Similarity	NPC3744
0.8904	High Similarity	NPC39361
0.8897	High Similarity	NPC105213
0.8897	High Similarity	NPC207732
0.8889	High Similarity	NPC312256
0.8867	High Similarity	NPC62051
0.8859	High Similarity	NPC78505
0.8859	High Similarity	NPC272566
0.8859	High Similarity	NPC124842
0.8859	High Similarity	NPC473201
0.8859	High Similarity	NPC302783
0.8859	High Similarity	NPC70320
0.8828	High Similarity	NPC16353
0.8819	High Similarity	NPC110419
0.8816	High Similarity	NPC167098
0.8816	High Similarity	NPC296044
0.8808	High Similarity	NPC39184
0.8808	High Similarity	NPC268008
0.8808	High Similarity	NPC130589
0.8808	High Similarity	NPC134287
0.8792	High Similarity	NPC472279
0.8776	High Similarity	NPC165389
0.8767	High Similarity	NPC91694
0.8767	High Similarity	NPC300603
0.8767	High Similarity	NPC113397
0.8766	High Similarity	NPC469889
0.8766	High Similarity	NPC131905
0.875	High Similarity	NPC213401
0.875	High Similarity	NPC326065
0.8733	High Similarity	NPC45291
0.8733	High Similarity	NPC19980
0.8733	High Similarity	NPC256406
0.8726	High Similarity	NPC186392
0.8725	High Similarity	NPC195763
0.8725	High Similarity	NPC264550
0.8725	High Similarity	NPC264289
0.8725	High Similarity	NPC333691
0.8725	High Similarity	NPC69430
0.8725	High Similarity	NPC40290
0.8725	High Similarity	NPC139293
0.8725	High Similarity	NPC142876
0.8725	High Similarity	NPC200060
0.8723	High Similarity	NPC144662
0.8705	High Similarity	NPC245395
0.8705	High Similarity	NPC66905
0.8701	High Similarity	NPC472962
0.8701	High Similarity	NPC472961
0.8693	High Similarity	NPC78103
0.8675	High Similarity	NPC100971
0.8675	High Similarity	NPC121522
0.8675	High Similarity	NPC291802
0.8675	High Similarity	NPC269451
0.8675	High Similarity	NPC216769
0.8675	High Similarity	NPC209487
0.8675	High Similarity	NPC131266
0.8675	High Similarity	NPC245382
0.8675	High Similarity	NPC100263
0.8675	High Similarity	NPC35763
0.8675	High Similarity	NPC181209
0.8662	High Similarity	NPC43065
0.8662	High Similarity	NPC139519
0.8662	High Similarity	NPC274613
0.8658	High Similarity	NPC166036
0.8658	High Similarity	NPC287395
0.8658	High Similarity	NPC183655
0.8658	High Similarity	NPC194653
0.8658	High Similarity	NPC203747
0.8658	High Similarity	NPC139364
0.8658	High Similarity	NPC254702
0.8658	High Similarity	NPC80710
0.8658	High Similarity	NPC238279
0.8658	High Similarity	NPC474903
0.8658	High Similarity	NPC203077
0.8652	High Similarity	NPC283823
0.8652	High Similarity	NPC159418
0.8652	High Similarity	NPC239855
0.8639	High Similarity	NPC142165
0.8636	High Similarity	NPC104876
0.8636	High Similarity	NPC245891
0.8636	High Similarity	NPC228501
0.863	High Similarity	NPC229218
0.863	High Similarity	NPC141817
0.863	High Similarity	NPC192597
0.863	High Similarity	NPC176030
0.863	High Similarity	NPC299154
0.863	High Similarity	NPC169214
0.8627	High Similarity	NPC5379
0.8627	High Similarity	NPC77807
0.8627	High Similarity	NPC14561
0.8623	High Similarity	NPC117237
0.8623	High Similarity	NPC203719
0.8621	High Similarity	NPC19158
0.8618	High Similarity	NPC124714
0.8618	High Similarity	NPC250557
0.8616	High Similarity	NPC131866
0.8609	High Similarity	NPC118427
0.8601	High Similarity	NPC475111
0.86	High Similarity	NPC38545
0.86	High Similarity	NPC102003
0.86	High Similarity	NPC171916
0.86	High Similarity	NPC92722
0.8592	High Similarity	NPC237330
0.8591	High Similarity	NPC472969
0.8591	High Similarity	NPC58373
0.8591	High Similarity	NPC188074
0.8591	High Similarity	NPC125449
0.8582	High Similarity	NPC111888
0.8581	High Similarity	NPC160777
0.8581	High Similarity	NPC141574
0.8581	High Similarity	NPC73416
0.8581	High Similarity	NPC84571
0.8571	High Similarity	NPC291508
0.8571	High Similarity	NPC37543
0.8571	High Similarity	NPC287722
0.8571	High Similarity	NPC199463
0.8571	High Similarity	NPC262286
0.8571	High Similarity	NPC469615
0.8571	High Similarity	NPC473090
0.8571	High Similarity	NPC299520
0.8571	High Similarity	NPC178976
0.8571	High Similarity	NPC254659
0.8571	High Similarity	NPC36852
0.8571	High Similarity	NPC143328
0.8571	High Similarity	NPC129684
0.8562	High Similarity	NPC230149
0.8562	High Similarity	NPC168247
0.8562	High Similarity	NPC117992
0.8562	High Similarity	NPC45849
0.8562	High Similarity	NPC200761
0.8562	High Similarity	NPC152951
0.8562	High Similarity	NPC470327
0.8562	High Similarity	NPC477503
0.8562	High Similarity	NPC57674
0.8561	High Similarity	NPC472968
0.8553	High Similarity	NPC471982
0.8553	High Similarity	NPC60211
0.8553	High Similarity	NPC295646
0.8553	High Similarity	NPC324233
0.8553	High Similarity	NPC323626
0.8553	High Similarity	NPC164912
0.8552	High Similarity	NPC474784
0.8543	High Similarity	NPC10467
0.8543	High Similarity	NPC239363
0.8543	High Similarity	NPC156953
0.8535	High Similarity	NPC18100
0.8533	High Similarity	NPC98809
0.8533	High Similarity	NPC476394
0.8533	High Similarity	NPC131451
0.8533	High Similarity	NPC15329
0.8531	High Similarity	NPC208760
0.8526	High Similarity	NPC311740
0.8526	High Similarity	NPC134783
0.8523	High Similarity	NPC12377
0.8516	High Similarity	NPC45846
0.8516	High Similarity	NPC55738
0.8514	High Similarity	NPC474982
0.8514	High Similarity	NPC309169
0.8514	High Similarity	NPC196941
0.8514	High Similarity	NPC469683
0.8514	High Similarity	NPC213900
0.8506	High Similarity	NPC470328
0.8506	High Similarity	NPC472455
0.8506	High Similarity	NPC472626
0.8506	High Similarity	NPC278778
0.8506	High Similarity	NPC109765
0.8506	High Similarity	NPC291878
0.8506	High Similarity	NPC195796
0.8506	High Similarity	NPC138243
0.8506	High Similarity	NPC209614
0.8506	High Similarity	NPC35038
0.8503	High Similarity	NPC284556
0.8503	High Similarity	NPC301178
0.8497	Intermediate Similarity	NPC469550
0.8497	Intermediate Similarity	NPC33051
0.8497	Intermediate Similarity	NPC107109
0.8497	Intermediate Similarity	NPC287504
0.8497	Intermediate Similarity	NPC227337
0.8497	Intermediate Similarity	NPC474000
0.8497	Intermediate Similarity	NPC25127
0.8497	Intermediate Similarity	NPC49402
0.8497	Intermediate Similarity	NPC93552
0.8497	Intermediate Similarity	NPC70433
0.8497	Intermediate Similarity	NPC273462
0.8493	Intermediate Similarity	NPC82336
0.8493	Intermediate Similarity	NPC78987
0.8491	Intermediate Similarity	NPC247973
0.8489	Intermediate Similarity	NPC21563
0.8489	Intermediate Similarity	NPC16651

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 NPC275278 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	963
0.2-0.3	1644
0.3-0.4	2650
0.4-0.5	1817
0.5-0.6	1024
0.6-0.7	568
0.7-0.8	130
0.8-0.85	13
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8623	High Similarity	NPD9494	Approved
0.8431	Intermediate Similarity	NPD1934	Approved
0.8377	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD3882	Suspended
0.8258	Intermediate Similarity	NPD2801	Approved
0.8239	Intermediate Similarity	NPD6232	Discontinued
0.8141	Intermediate Similarity	NPD1465	Phase 2
0.8086	Intermediate Similarity	NPD7473	Discontinued
0.8026	Intermediate Similarity	NPD1511	Approved
0.8014	Intermediate Similarity	NPD230	Phase 1
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7974	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD4380	Phase 2
0.7947	Intermediate Similarity	NPD4628	Phase 3
0.7943	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3818	Discontinued
0.7922	Intermediate Similarity	NPD1512	Approved
0.7919	Intermediate Similarity	NPD2935	Discontinued
0.7914	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6166	Phase 2
0.7914	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5494	Approved
0.7881	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1510	Phase 2
0.784	Intermediate Similarity	NPD1247	Approved
0.7836	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD943	Approved
0.7823	Intermediate Similarity	NPD1240	Approved
0.7792	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3817	Phase 2
0.7742	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3027	Phase 3
0.7725	Intermediate Similarity	NPD7074	Phase 3
0.7718	Intermediate Similarity	NPD1607	Approved
0.7716	Intermediate Similarity	NPD919	Approved
0.7679	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7054	Approved
0.7654	Intermediate Similarity	NPD7075	Discontinued
0.7632	Intermediate Similarity	NPD2344	Approved
0.7632	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2533	Approved
0.7628	Intermediate Similarity	NPD2532	Approved
0.7628	Intermediate Similarity	NPD2534	Approved
0.7619	Intermediate Similarity	NPD7472	Approved
0.7607	Intermediate Similarity	NPD6234	Discontinued
0.7582	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1549	Phase 2
0.7578	Intermediate Similarity	NPD7819	Suspended
0.7578	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6386	Approved
0.7562	Intermediate Similarity	NPD6385	Approved
0.7558	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6190	Approved
0.7547	Intermediate Similarity	NPD7458	Discontinued
0.7547	Intermediate Similarity	NPD3226	Approved
0.7533	Intermediate Similarity	NPD447	Suspended
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7529	Intermediate Similarity	NPD7685	Pre-registration
0.7516	Intermediate Similarity	NPD37	Approved
0.7516	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.7467	Intermediate Similarity	NPD1613	Approved
0.7467	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6799	Approved
0.7447	Intermediate Similarity	NPD5536	Phase 2
0.7439	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2309	Approved
0.7432	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7251	Discontinued
0.7425	Intermediate Similarity	NPD3926	Phase 2
0.7423	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD920	Approved
0.7419	Intermediate Similarity	NPD2800	Approved
0.7407	Intermediate Similarity	NPD6801	Discontinued
0.7405	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2346	Discontinued
0.7397	Intermediate Similarity	NPD1283	Approved
0.7394	Intermediate Similarity	NPD9545	Approved
0.7391	Intermediate Similarity	NPD6599	Discontinued
0.7391	Intermediate Similarity	NPD228	Approved
0.7386	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7808	Phase 3
0.7379	Intermediate Similarity	NPD3972	Approved
0.7379	Intermediate Similarity	NPD9269	Phase 2
0.7379	Intermediate Similarity	NPD1608	Approved
0.7378	Intermediate Similarity	NPD4966	Approved
0.7378	Intermediate Similarity	NPD4967	Phase 2
0.7378	Intermediate Similarity	NPD4965	Approved
0.7378	Intermediate Similarity	NPD7768	Phase 2
0.7372	Intermediate Similarity	NPD7003	Approved
0.7372	Intermediate Similarity	NPD3750	Approved
0.7351	Intermediate Similarity	NPD4060	Phase 1
0.7346	Intermediate Similarity	NPD7411	Suspended
0.7338	Intermediate Similarity	NPD2796	Approved
0.7338	Intermediate Similarity	NPD1551	Phase 2
0.7333	Intermediate Similarity	NPD3764	Approved
0.7333	Intermediate Similarity	NPD2313	Discontinued
0.7321	Intermediate Similarity	NPD5242	Approved
0.7296	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7228	Approved
0.7286	Intermediate Similarity	NPD5283	Phase 1
0.7278	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1470	Approved
0.7222	Intermediate Similarity	NPD1651	Approved
0.7219	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7199	Phase 2
0.7192	Intermediate Similarity	NPD1281	Approved
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7181	Intermediate Similarity	NPD2798	Approved
0.7172	Intermediate Similarity	NPD17	Approved
0.717	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1876	Approved
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6651	Approved
0.7134	Intermediate Similarity	NPD6873	Phase 2
0.7126	Intermediate Similarity	NPD3749	Approved
0.7125	Intermediate Similarity	NPD7390	Discontinued
0.7124	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2979	Phase 3
0.7124	Intermediate Similarity	NPD3620	Phase 2
0.7119	Intermediate Similarity	NPD8434	Phase 2
0.7118	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3455	Phase 2
0.7117	Intermediate Similarity	NPD824	Approved
0.7117	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5353	Approved
0.7108	Intermediate Similarity	NPD5402	Approved
0.7105	Intermediate Similarity	NPD6798	Discontinued
0.7103	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9268	Approved
0.7101	Intermediate Similarity	NPD8127	Discontinued
0.7095	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3751	Discontinued
0.7093	Intermediate Similarity	NPD7177	Discontinued
0.7089	Intermediate Similarity	NPD1243	Approved
0.7081	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1933	Approved
0.7075	Intermediate Similarity	NPD1201	Approved
0.707	Intermediate Similarity	NPD7266	Discontinued
0.7065	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5711	Approved
0.7059	Intermediate Similarity	NPD5710	Approved
0.7055	Intermediate Similarity	NPD4626	Approved
0.7051	Intermediate Similarity	NPD3748	Approved
0.7048	Intermediate Similarity	NPD8455	Phase 2
0.7045	Intermediate Similarity	NPD8312	Approved
0.7045	Intermediate Similarity	NPD8313	Approved
0.7044	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4110	Phase 3
0.7044	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2861	Phase 2
0.7019	Intermediate Similarity	NPD4357	Discontinued
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5978	Approved
0.7006	Intermediate Similarity	NPD6099	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD6100	Approved
0.7006	Intermediate Similarity	NPD5977	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7006	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD1203	Approved
0.7	Intermediate Similarity	NPD1164	Approved
0.7	Intermediate Similarity	NPD3021	Approved
0.7	Intermediate Similarity	NPD2354	Approved
0.7	Intermediate Similarity	NPD3022	Approved
0.6994	Remote Similarity	NPD2163	Approved
0.6993	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5953	Discontinued
0.6968	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7229	Phase 3
0.6959	Remote Similarity	NPD3705	Approved
0.6954	Remote Similarity	NPD7286	Phase 2
0.6951	Remote Similarity	NPD1653	Approved
0.6949	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4308	Phase 3
0.6933	Remote Similarity	NPD5049	Phase 3
0.6933	Remote Similarity	NPD6273	Approved
0.6932	Remote Similarity	NPD7038	Approved
0.6932	Remote Similarity	NPD7039	Approved
0.6927	Remote Similarity	NPD8150	Discontinued
0.6923	Remote Similarity	NPD1241	Discontinued
0.6918	Remote Similarity	NPD2424	Discontinued
0.6908	Remote Similarity	NPD3018	Phase 2
0.6905	Remote Similarity	NPD2296	Approved
0.6903	Remote Similarity	NPD1558	Phase 1
0.6899	Remote Similarity	NPD4476	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