NPASS Compound

Structure

NPC198038 OpenBabel07101719252D 34 36 0 0 0 0 0 0 0 0999 V2000 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 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 -3.4641 -0.0000 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 -6.0622 0.5000 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 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -6.0622 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 -6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 8 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 30 1 0 0 0 0 8 29 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 19 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 30 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 20 2 0 0 0 0 17 27 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 20 22 1 0 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 23 28 1 0 0 0 0 24 26 2 0 0 0 0 24 29 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 27 28 2 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.29
Volume:	515.836
LogP:	7.89
LogD:	4.893
LogS:	-2.3
# Rotatable Bonds:	8
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.366
Synthetic Accessibility Score:	3.428
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.17
MDCK Permeability:	1.6393767509725876e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	100.51758575439453%
Volume Distribution (VD):	4.657
Pgp-substrate:	0.9723663330078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.414
CYP1A2-substrate:	0.421
CYP2C19-inhibitor:	0.715
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.334
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.826
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	4.612
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.372
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.135
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.938
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.859
Respiratory Toxicity:	0.521

Download Data

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

Natural Product: NPC198038

Natural Product ID:	NPC198038
*Common Name:**	Kazinol D
IUPAC Name:	4-[3-[8-hydroxy-2,2-dimethyl-5-(3-methylbut-2-enyl)-3,4-dihydrochromen-6-yl]propyl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol
Synonyms:	Kazinol D
Standard InCHIKey:	ADFDRHICFIZUNK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H40O4/c1-8-29(4,5)24-16-21(25(31)18-26(24)32)11-9-10-20-17-27(33)28-23(14-15-30(6,7)34-28)22(20)13-12-19(2)3/h8,12,16-18,31-33H,1,9-11,13-15H2,2-7H3
SMILES:	C=CC(c1cc(CCCc2cc(O)c3c(c2CC=C(C)C)CCC(O3)(C)C)c(cc1O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454305
PubChem CID:	21637680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[11575957]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19046886]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20493686]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917310]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	3
IC50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	164700.0	nM	PMID[528589]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	200000.0	nM	PMID[528589]
NPT2428	Cell Line	HT-3	Homo sapiens	ED50	=	3.6	ug ml-1	PMID[528590]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.3	ug ml-1	PMID[528590]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	7.0	ug ml-1	PMID[528590]

☑ 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 NPC198038 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	492
0.1-0.2	1761
0.2-0.3	4399
0.3-0.4	12320
0.4-0.5	5876
0.5-0.6	3923
0.6-0.7	7633
0.7-0.8	5137
0.8-0.85	743
0.85-0.9	355
0.9-0.95	55
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.985	High Similarity	NPC234568
0.9489	High Similarity	NPC474104
0.9429	High Similarity	NPC473876
0.9343	High Similarity	NPC35216
0.9281	High Similarity	NPC473845
0.9281	High Similarity	NPC50250
0.9281	High Similarity	NPC469795
0.9248	High Similarity	NPC469907
0.9203	High Similarity	NPC71046
0.9197	High Similarity	NPC260741
0.9197	High Similarity	NPC32630
0.9197	High Similarity	NPC70682
0.9161	High Similarity	NPC195561
0.9149	High Similarity	NPC233980
0.9143	High Similarity	NPC473108
0.9137	High Similarity	NPC59841
0.9137	High Similarity	NPC475891
0.9137	High Similarity	NPC2613
0.9137	High Similarity	NPC204347
0.9124	High Similarity	NPC35550
0.9104	High Similarity	NPC15543
0.9097	High Similarity	NPC2745
0.9085	High Similarity	NPC474397
0.9065	High Similarity	NPC265075
0.9051	High Similarity	NPC265433
0.9051	High Similarity	NPC162659
0.9051	High Similarity	NPC227503
0.9051	High Similarity	NPC270456
0.9051	High Similarity	NPC474639
0.9051	High Similarity	NPC230734
0.9051	High Similarity	NPC234952
0.9051	High Similarity	NPC248727
0.9044	High Similarity	NPC317380
0.9037	High Similarity	NPC127624
0.9037	High Similarity	NPC86655
0.9037	High Similarity	NPC202762
0.9034	High Similarity	NPC157783
0.903	High Similarity	NPC126836
0.9028	High Similarity	NPC158784
0.9021	High Similarity	NPC212142
0.8993	High Similarity	NPC259519
0.8986	High Similarity	NPC56329
0.8986	High Similarity	NPC242715
0.8978	High Similarity	NPC112939
0.8978	High Similarity	NPC313081
0.8978	High Similarity	NPC473413
0.8978	High Similarity	NPC474206
0.8978	High Similarity	NPC151224
0.8978	High Similarity	NPC69029
0.8978	High Similarity	NPC158142
0.8978	High Similarity	NPC94750
0.8978	High Similarity	NPC121812
0.8978	High Similarity	NPC200557
0.8978	High Similarity	NPC108198
0.8978	High Similarity	NPC112246
0.8978	High Similarity	NPC241241
0.8978	High Similarity	NPC294884
0.8978	High Similarity	NPC10314
0.8978	High Similarity	NPC470356
0.8966	High Similarity	NPC302915
0.8947	High Similarity	NPC252131
0.8947	High Similarity	NPC470699
0.8921	High Similarity	NPC127218
0.8921	High Similarity	NPC19869
0.8921	High Similarity	NPC275061
0.8921	High Similarity	NPC319647
0.8921	High Similarity	NPC132804
0.8921	High Similarity	NPC25966
0.8921	High Similarity	NPC220344
0.8921	High Similarity	NPC243996
0.8921	High Similarity	NPC245207
0.8913	High Similarity	NPC202846
0.8913	High Similarity	NPC470802
0.8913	High Similarity	NPC302701
0.8913	High Similarity	NPC269091
0.8913	High Similarity	NPC306441
0.8913	High Similarity	NPC30632
0.8913	High Similarity	NPC16435
0.8913	High Similarity	NPC143139
0.8905	High Similarity	NPC209199
0.8905	High Similarity	NPC125649
0.8904	High Similarity	NPC160196
0.8904	High Similarity	NPC325860
0.8881	High Similarity	NPC226331
0.8881	High Similarity	NPC46274
0.8881	High Similarity	NPC211758
0.8881	High Similarity	NPC28765
0.8881	High Similarity	NPC87794
0.8873	High Similarity	NPC280092
0.8873	High Similarity	NPC93323
0.8873	High Similarity	NPC63879
0.8873	High Similarity	NPC45257
0.8873	High Similarity	NPC12641
0.8872	High Similarity	NPC181361
0.8865	High Similarity	NPC323126
0.8857	High Similarity	NPC309124
0.8857	High Similarity	NPC12668
0.8857	High Similarity	NPC308768
0.8857	High Similarity	NPC184797
0.8849	High Similarity	NPC230919
0.8849	High Similarity	NPC276490
0.8849	High Similarity	NPC266453
0.8849	High Similarity	NPC200935
0.8849	High Similarity	NPC22902
0.8849	High Similarity	NPC103976
0.8849	High Similarity	NPC211549
0.8849	High Similarity	NPC326797
0.8849	High Similarity	NPC102904
0.8849	High Similarity	NPC107551
0.8849	High Similarity	NPC474282
0.8849	High Similarity	NPC176051
0.8841	High Similarity	NPC234333
0.8841	High Similarity	NPC47398
0.8841	High Similarity	NPC164787
0.8841	High Similarity	NPC260898
0.8841	High Similarity	NPC61946
0.8832	High Similarity	NPC11060
0.8832	High Similarity	NPC229442
0.8832	High Similarity	NPC36661
0.8832	High Similarity	NPC475840
0.8832	High Similarity	NPC32778
0.8832	High Similarity	NPC168059
0.8819	High Similarity	NPC16269
0.8819	High Similarity	NPC21776
0.8811	High Similarity	NPC90645
0.8806	High Similarity	NPC74817
0.8806	High Similarity	NPC236791
0.8806	High Similarity	NPC124452
0.8806	High Similarity	NPC324112
0.8806	High Similarity	NPC282000
0.8806	High Similarity	NPC159968
0.8806	High Similarity	NPC169474
0.8806	High Similarity	NPC5447
0.8806	High Similarity	NPC293054
0.8806	High Similarity	NPC246620
0.8806	High Similarity	NPC210355
0.8806	High Similarity	NPC250432
0.8806	High Similarity	NPC82679
0.8803	High Similarity	NPC85264
0.8803	High Similarity	NPC47633
0.8803	High Similarity	NPC102044
0.8794	High Similarity	NPC263261
0.8794	High Similarity	NPC87725
0.8794	High Similarity	NPC471389
0.8788	High Similarity	NPC53567
0.8786	High Similarity	NPC236306
0.8786	High Similarity	NPC243759
0.8786	High Similarity	NPC79622
0.8786	High Similarity	NPC212942
0.8786	High Similarity	NPC105847
0.8786	High Similarity	NPC473739
0.8786	High Similarity	NPC184613
0.8786	High Similarity	NPC55947
0.8786	High Similarity	NPC29868
0.8786	High Similarity	NPC232164
0.8786	High Similarity	NPC218131
0.8784	High Similarity	NPC80918
0.8784	High Similarity	NPC188578
0.8777	High Similarity	NPC173660
0.8768	High Similarity	NPC160697
0.8768	High Similarity	NPC66840
0.8768	High Similarity	NPC478085
0.8768	High Similarity	NPC256307
0.8759	High Similarity	NPC14224
0.8759	High Similarity	NPC161958
0.875	High Similarity	NPC260397
0.875	High Similarity	NPC474481
0.875	High Similarity	NPC91291
0.8741	High Similarity	NPC277951
0.8741	High Similarity	NPC317237
0.8741	High Similarity	NPC154866
0.8741	High Similarity	NPC44530
0.8732	High Similarity	NPC183709
0.8732	High Similarity	NPC107161
0.8732	High Similarity	NPC175838
0.8731	High Similarity	NPC18924
0.8731	High Similarity	NPC44748
0.8731	High Similarity	NPC214406
0.8731	High Similarity	NPC78974
0.8731	High Similarity	NPC223136
0.8731	High Similarity	NPC103823
0.8731	High Similarity	NPC28730
0.8723	High Similarity	NPC472092
0.8723	High Similarity	NPC472090
0.8723	High Similarity	NPC472091
0.8723	High Similarity	NPC109240
0.8722	High Similarity	NPC122792
0.8722	High Similarity	NPC228972
0.8714	High Similarity	NPC94994
0.8714	High Similarity	NPC266006
0.8714	High Similarity	NPC151656
0.8705	High Similarity	NPC180602
0.8705	High Similarity	NPC55239
0.8705	High Similarity	NPC214853
0.8705	High Similarity	NPC327382
0.8705	High Similarity	NPC256262
0.8705	High Similarity	NPC195022
0.8705	High Similarity	NPC240279
0.8699	High Similarity	NPC476969
0.8696	High Similarity	NPC263064

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 NPC198038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	967
0.2-0.3	1747
0.3-0.4	2815
0.4-0.5	1572
0.5-0.6	878
0.6-0.7	620
0.7-0.8	123
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD1529	Clinical (unspecified phase)
0.8806	High Similarity	NPD1530	Clinical (unspecified phase)
0.8676	High Similarity	NPD4625	Phase 3
0.8623	High Similarity	NPD1612	Clinical (unspecified phase)
0.8623	High Similarity	NPD1613	Approved
0.8406	Intermediate Similarity	NPD3027	Phase 3
0.8345	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD4908	Phase 1
0.8102	Intermediate Similarity	NPD4749	Approved
0.8088	Intermediate Similarity	NPD1610	Phase 2
0.7972	Intermediate Similarity	NPD4060	Phase 1
0.7945	Intermediate Similarity	NPD6099	Approved
0.7945	Intermediate Similarity	NPD6100	Approved
0.7935	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1934	Approved
0.7847	Intermediate Similarity	NPD3620	Phase 2
0.7847	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1548	Phase 1
0.7786	Intermediate Similarity	NPD6696	Suspended
0.7786	Intermediate Similarity	NPD8651	Approved
0.7785	Intermediate Similarity	NPD6674	Discontinued
0.7785	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD7095	Approved
0.7746	Intermediate Similarity	NPD3018	Phase 2
0.7733	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2801	Approved
0.7704	Intermediate Similarity	NPD6671	Approved
0.7687	Intermediate Similarity	NPD5283	Phase 1
0.7676	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD228	Approved
0.7625	Intermediate Similarity	NPD6234	Discontinued
0.7622	Intermediate Similarity	NPD2861	Phase 2
0.7595	Intermediate Similarity	NPD1465	Phase 2
0.7589	Intermediate Similarity	NPD2983	Phase 2
0.7589	Intermediate Similarity	NPD2982	Phase 2
0.7582	Intermediate Similarity	NPD1511	Approved
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7574	Intermediate Similarity	NPD7157	Approved
0.7551	Intermediate Similarity	NPD5735	Approved
0.7531	Intermediate Similarity	NPD7199	Phase 2
0.7519	Intermediate Similarity	NPD3022	Approved
0.7519	Intermediate Similarity	NPD3021	Approved
0.7518	Intermediate Similarity	NPD2981	Phase 2
0.7515	Intermediate Similarity	NPD8053	Approved
0.7515	Intermediate Similarity	NPD8054	Approved
0.7515	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6232	Discontinued
0.7484	Intermediate Similarity	NPD1512	Approved
0.7484	Intermediate Similarity	NPD7819	Suspended
0.7483	Intermediate Similarity	NPD1558	Phase 1
0.7465	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7473	Discontinued
0.7439	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7074	Phase 3
0.7421	Intermediate Similarity	NPD37	Approved
0.7394	Intermediate Similarity	NPD2489	Approved
0.7394	Intermediate Similarity	NPD27	Approved
0.7391	Intermediate Similarity	NPD4966	Approved
0.7391	Intermediate Similarity	NPD7340	Approved
0.7391	Intermediate Similarity	NPD4965	Approved
0.7391	Intermediate Similarity	NPD4967	Phase 2
0.7386	Intermediate Similarity	NPD3750	Approved
0.7384	Intermediate Similarity	NPD7906	Approved
0.7383	Intermediate Similarity	NPD4097	Suspended
0.7365	Intermediate Similarity	NPD7054	Approved
0.7358	Intermediate Similarity	NPD6072	Discontinued
0.7353	Intermediate Similarity	NPD7311	Approved
0.7353	Intermediate Similarity	NPD7313	Approved
0.7353	Intermediate Similarity	NPD7312	Approved
0.7353	Intermediate Similarity	NPD7310	Approved
0.7347	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7075	Discontinued
0.7343	Intermediate Similarity	NPD5327	Phase 3
0.7333	Intermediate Similarity	NPD4536	Approved
0.7333	Intermediate Similarity	NPD4538	Approved
0.7333	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD422	Phase 1
0.7321	Intermediate Similarity	NPD7472	Approved
0.7315	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5124	Phase 1
0.731	Intermediate Similarity	NPD7309	Approved
0.7308	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7447	Phase 1
0.7303	Intermediate Similarity	NPD5763	Approved
0.7303	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5762	Approved
0.7299	Intermediate Similarity	NPD1398	Phase 1
0.729	Intermediate Similarity	NPD7124	Phase 2
0.7267	Intermediate Similarity	NPD6353	Approved
0.7267	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5494	Approved
0.7251	Intermediate Similarity	NPD4577	Approved
0.7251	Intermediate Similarity	NPD4578	Approved
0.7233	Intermediate Similarity	NPD4005	Discontinued
0.7229	Intermediate Similarity	NPD2970	Approved
0.7229	Intermediate Similarity	NPD2969	Approved
0.7226	Intermediate Similarity	NPD7843	Approved
0.7225	Intermediate Similarity	NPD4663	Approved
0.7222	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3817	Phase 2
0.7203	Intermediate Similarity	NPD3705	Approved
0.7202	Intermediate Similarity	NPD3818	Discontinued
0.7197	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4624	Approved
0.719	Intermediate Similarity	NPD3540	Phase 1
0.7188	Intermediate Similarity	NPD4380	Phase 2
0.7185	Intermediate Similarity	NPD2684	Approved
0.7183	Intermediate Similarity	NPD4626	Approved
0.7171	Intermediate Similarity	NPD5588	Approved
0.7171	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5960	Phase 3
0.7171	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD3051	Approved
0.7169	Intermediate Similarity	NPD6071	Discontinued
0.7161	Intermediate Similarity	NPD6331	Phase 2
0.7161	Intermediate Similarity	NPD3892	Phase 2
0.716	Intermediate Similarity	NPD5929	Approved
0.7135	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD7213	Phase 3
0.7134	Intermediate Similarity	NPD7041	Phase 2
0.7134	Intermediate Similarity	NPD7831	Phase 2
0.7134	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7212	Phase 2
0.7134	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7833	Phase 2
0.7133	Intermediate Similarity	NPD4140	Approved
0.7132	Intermediate Similarity	NPD4750	Phase 3
0.7124	Intermediate Similarity	NPD3539	Phase 1
0.7121	Intermediate Similarity	NPD940	Approved
0.7121	Intermediate Similarity	NPD846	Approved
0.7117	Intermediate Similarity	NPD2560	Approved
0.7117	Intermediate Similarity	NPD2563	Approved
0.7115	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6959	Discontinued
0.7105	Intermediate Similarity	NPD6111	Discontinued
0.7101	Intermediate Similarity	NPD8099	Discontinued
0.7101	Intermediate Similarity	NPD8251	Approved
0.7101	Intermediate Similarity	NPD8252	Approved
0.7093	Intermediate Similarity	NPD7808	Phase 3
0.7093	Intermediate Similarity	NPD7549	Discontinued
0.7086	Intermediate Similarity	NPD6355	Discontinued
0.7086	Intermediate Similarity	NPD3657	Discovery
0.7083	Intermediate Similarity	NPD1611	Approved
0.7083	Intermediate Similarity	NPD1091	Approved
0.7081	Intermediate Similarity	NPD4675	Approved
0.7081	Intermediate Similarity	NPD4678	Approved
0.7078	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7266	Discontinued
0.7078	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6797	Phase 2
0.7075	Intermediate Similarity	NPD6584	Phase 3
0.7073	Intermediate Similarity	NPD7768	Phase 2
0.707	Intermediate Similarity	NPD5058	Phase 3
0.7066	Intermediate Similarity	NPD7229	Phase 3
0.7059	Intermediate Similarity	NPD8156	Discontinued
0.7059	Intermediate Similarity	NPD3748	Approved
0.7051	Intermediate Similarity	NPD7466	Approved
0.7051	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4110	Phase 3
0.7045	Intermediate Similarity	NPD1242	Phase 1
0.7037	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7240	Approved
0.7032	Intermediate Similarity	NPD2424	Discontinued
0.7032	Intermediate Similarity	NPD1549	Phase 2
0.703	Intermediate Similarity	NPD4055	Discovery
0.703	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2797	Approved
0.7007	Intermediate Similarity	NPD3094	Phase 2
0.7006	Intermediate Similarity	NPD8127	Discontinued
0.7006	Intermediate Similarity	NPD2677	Approved
0.7	Intermediate Similarity	NPD5111	Phase 2
0.7	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD5110	Phase 2
0.7	Intermediate Similarity	NPD5109	Approved
0.6994	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5691	Approved
0.6993	Remote Similarity	NPD1357	Approved
0.6987	Remote Similarity	NPD5177	Phase 3
0.6987	Remote Similarity	NPD1652	Phase 2
0.6985	Remote Similarity	NPD290	Approved
0.6981	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5535	Approved
0.6978	Remote Similarity	NPD7635	Approved
0.6978	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7993	Clinical (unspecified phase)

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