NPASS Compound

Structure

NPC475095 OpenBabel07101719142D 27 31 0 0 1 0 0 0 0 0999 V2000 2.3479 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6324 3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8025 2.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8135 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.7045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2202 2.7406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 1.1226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6342 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6342 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 20 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 11 2 0 0 0 0 6 16 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 26 1 0 0 0 0 9 27 1 0 0 0 0 10 20 1 1 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 21 1 6 0 0 0 21 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.14
Volume:	365.912
LogP:	2.514
LogD:	2.734
LogS:	-4.129
# Rotatable Bonds:	2
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.863
Synthetic Accessibility Score:	5.114
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	1.8531576642999426e-05
Pgp-inhibitor:	0.286
Pgp-substrate:	0.237
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.906
30% Bioavailability (F30%):	0.107

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.311
Plasma Protein Binding (PPB):	92.20027160644531%
Volume Distribution (VD):	1.658
Pgp-substrate:	9.685017585754395%

ADMET: Metabolism

CYP1A2-inhibitor:	0.924
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.965
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.883
CYP2C9-substrate:	0.242
CYP2D6-inhibitor:	0.901
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.943
CYP3A4-substrate:	0.9

ADMET: Excretion

Clearance (CL):	6.637
Half-life (T1/2):	0.306

ADMET: Toxicity

hERG Blockers:	0.154
Human Hepatotoxicity (H-HT):	0.752
Drug-inuced Liver Injury (DILI):	0.499
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.571
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC475095

Natural Product ID:	NPC475095
*Common Name:**	Kadsulignan K
IUPAC Name:	n.a.
Synonyms:	Kadsulignan K
Standard InCHIKey:	YINXUXPKOPNKJP-ZADZRWDBSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-10-5-11-6-16(24-3)17(25-4)19(23)21(11)13-8-15-14(26-9-27-15)7-12(13)18(22)20(10,21)2/h6-8,10,18,22H,5,9H2,1-4H3/t10-,18+,20+,21-/m1/s1
SMILES:	CC1CC2=CC(=C(C(=O)C23C1(C(C4=CC5=C(C=C34)OCO5)O)C)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497452
PubChem CID:	44583791
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16018647]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16018647]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[16268562]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792420]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17608535]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	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
ED50	3
Others	1

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>=	5.0	ug ml-1	PMID[508056]
NPT91	Cell Line	KB	Homo sapiens	ED50	>=	5.0	ug ml-1	PMID[508056]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>=	5.0	ug ml-1	PMID[508056]
NPT1	Others	Radical scavenging activity		Activity	=	4.6	%	PMID[508056]

☑ 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 NPC475095 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	361
0.1-0.2	1429
0.2-0.3	3005
0.3-0.4	6829
0.4-0.5	11381
0.5-0.6	6290
0.6-0.7	10882
0.7-0.8	2465
0.8-0.85	44
0.85-0.9	8
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8734	High Similarity	NPC476364
0.8659	High Similarity	NPC476277
0.8645	High Similarity	NPC476336
0.8634	High Similarity	NPC472565
0.8627	High Similarity	NPC472564
0.8589	High Similarity	NPC476244
0.8544	High Similarity	NPC163002
0.8535	High Similarity	NPC472567
0.8526	High Similarity	NPC25496
0.8481	Intermediate Similarity	NPC12854
0.8466	Intermediate Similarity	NPC476337
0.8447	Intermediate Similarity	NPC476363
0.8405	Intermediate Similarity	NPC68619
0.8365	Intermediate Similarity	NPC475170
0.8312	Intermediate Similarity	NPC470855
0.8291	Intermediate Similarity	NPC476338
0.8291	Intermediate Similarity	NPC476359
0.8261	Intermediate Similarity	NPC28724
0.8232	Intermediate Similarity	NPC476340
0.8204	Intermediate Similarity	NPC475865
0.8199	Intermediate Similarity	NPC178048
0.8194	Intermediate Similarity	NPC322021
0.8194	Intermediate Similarity	NPC278076
0.8182	Intermediate Similarity	NPC179914
0.8166	Intermediate Similarity	NPC474948
0.8166	Intermediate Similarity	NPC42230
0.8137	Intermediate Similarity	NPC177830
0.8133	Intermediate Similarity	NPC218471
0.8133	Intermediate Similarity	NPC239818
0.8113	Intermediate Similarity	NPC3982
0.8113	Intermediate Similarity	NPC472560
0.8101	Intermediate Similarity	NPC15743
0.8095	Intermediate Similarity	NPC100420
0.8047	Intermediate Similarity	NPC475953
0.8047	Intermediate Similarity	NPC474647
0.8038	Intermediate Similarity	NPC474966
0.8037	Intermediate Similarity	NPC476335
0.8036	Intermediate Similarity	NPC476011
0.8025	Intermediate Similarity	NPC28398
0.8025	Intermediate Similarity	NPC51681
0.8024	Intermediate Similarity	NPC474770
0.8024	Intermediate Similarity	NPC474936
0.8012	Intermediate Similarity	NPC304821
0.8	Intermediate Similarity	NPC30890
0.8	Intermediate Similarity	NPC189054
0.8	Intermediate Similarity	NPC476362
0.7988	Intermediate Similarity	NPC44730
0.7988	Intermediate Similarity	NPC469475
0.7988	Intermediate Similarity	NPC469518
0.7987	Intermediate Similarity	NPC50696
0.7987	Intermediate Similarity	NPC46880
0.7987	Intermediate Similarity	NPC37065
0.7977	Intermediate Similarity	NPC474568
0.7976	Intermediate Similarity	NPC99968
0.7975	Intermediate Similarity	NPC476840
0.7975	Intermediate Similarity	NPC104956
0.7975	Intermediate Similarity	NPC476842
0.7964	Intermediate Similarity	NPC76211
0.7963	Intermediate Similarity	NPC161955
0.7961	Intermediate Similarity	NPC477694
0.7961	Intermediate Similarity	NPC477705
0.795	Intermediate Similarity	NPC153620
0.795	Intermediate Similarity	NPC24257
0.7949	Intermediate Similarity	NPC166184
0.7937	Intermediate Similarity	NPC327052
0.7929	Intermediate Similarity	NPC326278
0.7929	Intermediate Similarity	NPC206815
0.7921	Intermediate Similarity	NPC299855
0.7921	Intermediate Similarity	NPC96194
0.7908	Intermediate Similarity	NPC477706
0.7907	Intermediate Similarity	NPC21956
0.7904	Intermediate Similarity	NPC220462
0.7904	Intermediate Similarity	NPC474990
0.7901	Intermediate Similarity	NPC98009
0.7898	Intermediate Similarity	NPC178290
0.7895	Intermediate Similarity	NPC130730
0.7895	Intermediate Similarity	NPC301910
0.7892	Intermediate Similarity	NPC254163
0.7892	Intermediate Similarity	NPC38699
0.7892	Intermediate Similarity	NPC475484
0.7882	Intermediate Similarity	NPC327694
0.7882	Intermediate Similarity	NPC100425
0.7879	Intermediate Similarity	NPC245948
0.7879	Intermediate Similarity	NPC308555
0.7879	Intermediate Similarity	NPC327225
0.7877	Intermediate Similarity	NPC189704
0.7874	Intermediate Similarity	NPC473467
0.7874	Intermediate Similarity	NPC475197
0.7866	Intermediate Similarity	NPC475379
0.7857	Intermediate Similarity	NPC259742
0.7857	Intermediate Similarity	NPC219671
0.7857	Intermediate Similarity	NPC104077
0.7857	Intermediate Similarity	NPC147616
0.7849	Intermediate Similarity	NPC471180
0.7844	Intermediate Similarity	NPC237946
0.7844	Intermediate Similarity	NPC32373
0.7844	Intermediate Similarity	NPC48105
0.7836	Intermediate Similarity	NPC475738
0.7836	Intermediate Similarity	NPC318472
0.7834	Intermediate Similarity	NPC52968
0.7834	Intermediate Similarity	NPC231719
0.7833	Intermediate Similarity	NPC476067
0.7833	Intermediate Similarity	NPC475121
0.7829	Intermediate Similarity	NPC469438
0.7826	Intermediate Similarity	NPC469683
0.7826	Intermediate Similarity	NPC476841
0.7826	Intermediate Similarity	NPC476843
0.7821	Intermediate Similarity	NPC174191
0.7818	Intermediate Similarity	NPC220577
0.7818	Intermediate Similarity	NPC56184
0.7818	Intermediate Similarity	NPC151425
0.7812	Intermediate Similarity	NPC86455
0.7812	Intermediate Similarity	NPC125134
0.7812	Intermediate Similarity	NPC137920
0.7809	Intermediate Similarity	NPC473205
0.7809	Intermediate Similarity	NPC473776
0.7805	Intermediate Similarity	NPC205054
0.7802	Intermediate Similarity	NPC475299
0.7799	Intermediate Similarity	NPC323601
0.7798	Intermediate Similarity	NPC19947
0.7798	Intermediate Similarity	NPC207584
0.7797	Intermediate Similarity	NPC93685
0.7797	Intermediate Similarity	NPC108191
0.7791	Intermediate Similarity	NPC200726
0.7791	Intermediate Similarity	NPC282551
0.779	Intermediate Similarity	NPC71385
0.779	Intermediate Similarity	NPC230670
0.7784	Intermediate Similarity	NPC23593
0.7784	Intermediate Similarity	NPC117154
0.7778	Intermediate Similarity	NPC476822
0.7778	Intermediate Similarity	NPC173729
0.7778	Intermediate Similarity	NPC272750
0.7778	Intermediate Similarity	NPC134047
0.7778	Intermediate Similarity	NPC223006
0.7778	Intermediate Similarity	NPC87295
0.7765	Intermediate Similarity	NPC288149
0.7764	Intermediate Similarity	NPC46161
0.7764	Intermediate Similarity	NPC469615
0.7764	Intermediate Similarity	NPC239608
0.7759	Intermediate Similarity	NPC135370
0.7758	Intermediate Similarity	NPC62354
0.7758	Intermediate Similarity	NPC164082
0.7756	Intermediate Similarity	NPC45404
0.7753	Intermediate Similarity	NPC170203
0.7751	Intermediate Similarity	NPC477410
0.7751	Intermediate Similarity	NPC325122
0.775	Intermediate Similarity	NPC52664
0.7747	Intermediate Similarity	NPC112708
0.7746	Intermediate Similarity	NPC177362
0.7744	Intermediate Similarity	NPC474556
0.7744	Intermediate Similarity	NPC477698
0.7742	Intermediate Similarity	NPC239302
0.7738	Intermediate Similarity	NPC109765
0.7738	Intermediate Similarity	NPC261090
0.7738	Intermediate Similarity	NPC163635
0.7738	Intermediate Similarity	NPC477380
0.7736	Intermediate Similarity	NPC147379
0.7733	Intermediate Similarity	NPC474301
0.7733	Intermediate Similarity	NPC180586
0.7727	Intermediate Similarity	NPC107739
0.7727	Intermediate Similarity	NPC475244
0.7725	Intermediate Similarity	NPC136757
0.7725	Intermediate Similarity	NPC25127
0.7725	Intermediate Similarity	NPC62051
0.7725	Intermediate Similarity	NPC287504
0.7719	Intermediate Similarity	NPC76687
0.7719	Intermediate Similarity	NPC469512
0.7719	Intermediate Similarity	NPC164937
0.7719	Intermediate Similarity	NPC144557
0.7719	Intermediate Similarity	NPC145847
0.7714	Intermediate Similarity	NPC471181
0.7714	Intermediate Similarity	NPC469506
0.7711	Intermediate Similarity	NPC203664
0.7707	Intermediate Similarity	NPC18576
0.7707	Intermediate Similarity	NPC139519
0.7706	Intermediate Similarity	NPC268718
0.7706	Intermediate Similarity	NPC150943
0.7706	Intermediate Similarity	NPC139876
0.7706	Intermediate Similarity	NPC91634
0.7706	Intermediate Similarity	NPC119910
0.7706	Intermediate Similarity	NPC472961
0.7706	Intermediate Similarity	NPC96593
0.7706	Intermediate Similarity	NPC472962
0.7705	Intermediate Similarity	NPC473711
0.7701	Intermediate Similarity	NPC202428
0.7701	Intermediate Similarity	NPC266545
0.7697	Intermediate Similarity	NPC227980
0.7697	Intermediate Similarity	NPC158635
0.7697	Intermediate Similarity	NPC229882
0.7697	Intermediate Similarity	NPC236089
0.7692	Intermediate Similarity	NPC477885
0.7692	Intermediate Similarity	NPC473395
0.7692	Intermediate Similarity	NPC84935
0.7692	Intermediate Similarity	NPC286919
0.7692	Intermediate Similarity	NPC202495
0.7692	Intermediate Similarity	NPC190020
0.7692	Intermediate Similarity	NPC475663
0.7692	Intermediate Similarity	NPC129889
0.7692	Intermediate Similarity	NPC307006
0.7692	Intermediate Similarity	NPC77679

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 NPC475095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	873
0.2-0.3	1850
0.3-0.4	2683
0.4-0.5	1983
0.5-0.6	1045
0.6-0.7	360
0.7-0.8	33
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8199	Intermediate Similarity	NPD7028	Phase 2
0.7937	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD37	Approved
0.7844	Intermediate Similarity	NPD4966	Approved
0.7844	Intermediate Similarity	NPD4965	Approved
0.7844	Intermediate Similarity	NPD4967	Phase 2
0.7797	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7199	Phase 2
0.767	Intermediate Similarity	NPD7685	Pre-registration
0.7647	Intermediate Similarity	NPD6234	Discontinued
0.7483	Intermediate Similarity	NPD3705	Approved
0.7443	Intermediate Similarity	NPD3818	Discontinued
0.7443	Intermediate Similarity	NPD7228	Approved
0.7405	Intermediate Similarity	NPD3620	Phase 2
0.7405	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8127	Discontinued
0.7326	Intermediate Similarity	NPD3882	Suspended
0.7317	Intermediate Similarity	NPD4628	Phase 3
0.7285	Intermediate Similarity	NPD1357	Approved
0.7278	Intermediate Similarity	NPD6764	Approved
0.7278	Intermediate Similarity	NPD6765	Approved
0.7239	Intermediate Similarity	NPD5763	Approved
0.7239	Intermediate Similarity	NPD5762	Approved
0.7238	Intermediate Similarity	NPD7808	Phase 3
0.7238	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6797	Phase 2
0.7212	Intermediate Similarity	NPD4110	Phase 3
0.7212	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6273	Approved
0.7182	Intermediate Similarity	NPD7240	Approved
0.7182	Intermediate Similarity	NPD7251	Discontinued
0.7167	Intermediate Similarity	NPD7074	Phase 3
0.7151	Intermediate Similarity	NPD7799	Discontinued
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.712	Intermediate Similarity	NPD6785	Approved
0.712	Intermediate Similarity	NPD6784	Approved
0.7111	Intermediate Similarity	NPD7054	Approved
0.7095	Intermediate Similarity	NPD7473	Discontinued
0.7076	Intermediate Similarity	NPD7458	Discontinued
0.7072	Intermediate Similarity	NPD7472	Approved
0.7069	Intermediate Similarity	NPD3817	Phase 2
0.7066	Intermediate Similarity	NPD6190	Approved
0.7052	Intermediate Similarity	NPD1934	Approved
0.7039	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6166	Phase 2
0.7039	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD5735	Approved
0.703	Intermediate Similarity	NPD6005	Phase 3
0.703	Intermediate Similarity	NPD6002	Phase 3
0.703	Intermediate Similarity	NPD6004	Phase 3
0.703	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD3787	Discontinued
0.7022	Intermediate Similarity	NPD6232	Discontinued
0.7019	Intermediate Similarity	NPD6663	Approved
0.7017	Intermediate Similarity	NPD5844	Phase 1
0.7011	Intermediate Similarity	NPD5760	Phase 2
0.7011	Intermediate Similarity	NPD5761	Phase 2
0.7006	Intermediate Similarity	NPD5494	Approved
0.7005	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8434	Phase 2
0.6981	Remote Similarity	NPD9494	Approved
0.6975	Remote Similarity	NPD4140	Approved
0.6941	Remote Similarity	NPD2532	Approved
0.6941	Remote Similarity	NPD2533	Approved
0.6941	Remote Similarity	NPD2534	Approved
0.6941	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3657	Discovery
0.6932	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7296	Approved
0.6923	Remote Similarity	NPD7236	Approved
0.6923	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5647	Approved
0.6914	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2801	Approved
0.6899	Remote Similarity	NPD1876	Approved
0.6894	Remote Similarity	NPD3027	Phase 3
0.6893	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6653	Approved
0.6886	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5978	Approved
0.6875	Remote Similarity	NPD5977	Approved
0.6854	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6674	Discontinued
0.6839	Remote Similarity	NPD6599	Discontinued
0.6835	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD230	Phase 1
0.6805	Remote Similarity	NPD8166	Discontinued
0.6795	Remote Similarity	NPD2932	Approved
0.6788	Remote Similarity	NPD6353	Approved
0.6786	Remote Similarity	NPD3057	Approved
0.6778	Remote Similarity	NPD1247	Approved
0.6772	Remote Similarity	NPD1608	Approved
0.677	Remote Similarity	NPD5736	Approved
0.6768	Remote Similarity	NPD4060	Phase 1
0.676	Remote Similarity	NPD919	Approved
0.6746	Remote Similarity	NPD2800	Approved
0.6744	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3146	Approved
0.674	Remote Similarity	NPD7315	Approved
0.6738	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7266	Discontinued
0.6724	Remote Similarity	NPD7239	Suspended
0.6723	Remote Similarity	NPD1465	Phase 2
0.6723	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6559	Discontinued
0.6718	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5536	Phase 2
0.6708	Remote Similarity	NPD4624	Approved
0.6707	Remote Similarity	NPD8032	Phase 2
0.6705	Remote Similarity	NPD6385	Approved
0.6705	Remote Similarity	NPD1512	Approved
0.6705	Remote Similarity	NPD6386	Approved
0.6704	Remote Similarity	NPD7075	Discontinued
0.6703	Remote Similarity	NPD3926	Phase 2
0.6702	Remote Similarity	NPD2490	Approved
0.6702	Remote Similarity	NPD2488	Approved
0.6701	Remote Similarity	NPD2973	Approved
0.6701	Remote Similarity	NPD3533	Approved
0.6701	Remote Similarity	NPD2974	Approved
0.6701	Remote Similarity	NPD2975	Approved
0.6701	Remote Similarity	NPD2972	Approved
0.6688	Remote Similarity	NPD3019	Approved
0.6687	Remote Similarity	NPD1283	Approved
0.6687	Remote Similarity	NPD7095	Approved
0.6686	Remote Similarity	NPD6799	Approved
0.6685	Remote Similarity	NPD5353	Approved
0.6684	Remote Similarity	NPD4580	Approved
0.6667	Remote Similarity	NPD7680	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD5283	Phase 1
0.6667	Remote Similarity	NPD6100	Approved
0.665	Remote Similarity	NPD2493	Approved
0.665	Remote Similarity	NPD2494	Approved
0.6649	Remote Similarity	NPD2968	Approved
0.6649	Remote Similarity	NPD8313	Approved
0.6649	Remote Similarity	NPD2971	Approved
0.6649	Remote Similarity	NPD8312	Approved
0.6648	Remote Similarity	NPD4380	Phase 2
0.6647	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6798	Discontinued
0.6646	Remote Similarity	NPD3094	Phase 2
0.6646	Remote Similarity	NPD3764	Approved
0.6633	Remote Similarity	NPD4583	Approved
0.6633	Remote Similarity	NPD4582	Approved
0.6629	Remote Similarity	NPD7819	Suspended
0.6629	Remote Similarity	NPD1653	Approved
0.6625	Remote Similarity	NPD5327	Phase 3
0.6608	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6233	Phase 2
0.6605	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3092	Approved
0.6599	Remote Similarity	NPD6782	Approved
0.6599	Remote Similarity	NPD6780	Approved
0.6599	Remote Similarity	NPD6776	Approved
0.6599	Remote Similarity	NPD6779	Approved
0.6599	Remote Similarity	NPD6781	Approved
0.6599	Remote Similarity	NPD6778	Approved
0.6599	Remote Similarity	NPD6777	Approved
0.6599	Remote Similarity	NPD4107	Approved
0.6595	Remote Similarity	NPD2163	Approved
0.6592	Remote Similarity	NPD5402	Approved
0.659	Remote Similarity	NPD1511	Approved
0.6588	Remote Similarity	NPD4534	Discontinued
0.6588	Remote Similarity	NPD5958	Discontinued
0.6583	Remote Similarity	NPD7435	Discontinued
0.6583	Remote Similarity	NPD4002	Approved
0.6583	Remote Similarity	NPD7497	Discontinued
0.6583	Remote Similarity	NPD4004	Approved
0.6582	Remote Similarity	NPD17	Approved
0.6568	Remote Similarity	NPD2438	Suspended
0.6566	Remote Similarity	NPD2979	Phase 3
0.6566	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3450	Approved
0.6566	Remote Similarity	NPD3452	Approved
0.6564	Remote Similarity	NPD2861	Phase 2
0.6561	Remote Similarity	NPD3091	Approved
0.6536	Remote Similarity	NPD8455	Phase 2
0.6533	Remote Similarity	NPD2491	Approved
0.6527	Remote Similarity	NPD447	Suspended
0.6522	Remote Similarity	NPD5242	Approved
0.652	Remote Similarity	NPD5676	Approved
0.6519	Remote Similarity	NPD1651	Approved
0.6512	Remote Similarity	NPD3750	Approved
0.6512	Remote Similarity	NPD7003	Approved
0.6509	Remote Similarity	NPD7033	Discontinued
0.6509	Remote Similarity	NPD1510	Phase 2
0.6509	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4062	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