NPASS Compound

Structure

CID126556 OpenBabel06191715482D 29 33 0 0 1 0 0 0 0 0999 V2000 1.6544 2.5263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3573 2.1519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7585 5.0370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6644 1.7650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3705 0.0619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5062 0.8111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3125 0.7573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9314 -0.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0497 0.9159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0498 2.7888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0051 2.3210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1944 2.7890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2385 1.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2386 2.3208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8604 1.3840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8604 2.3207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7002 -0.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6168 2.3209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1944 3.7252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1945 0.9161 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0051 1.3843 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6167 1.3842 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4280 2.7889 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6621 0.9212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7445 -1.2801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9518 4.2753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6712 2.7887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6607 4.1060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 5 6 2 0 0 0 0 5 17 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 8 24 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 24 1 0 0 0 0 17 26 2 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 20 21 1 6 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 4 1 1 0 0 0 22 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.17
Volume:	393.775
LogP:	1.472
LogD:	1.565
LogS:	-3.477
# Rotatable Bonds:	4
TPSA:	88.43
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.793
Synthetic Accessibility Score:	5.198
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.912
MDCK Permeability:	2.1390440451796167e-05
Pgp-inhibitor:	0.535
Pgp-substrate:	0.607
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.668

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.939
Plasma Protein Binding (PPB):	81.19943237304688%
Volume Distribution (VD):	0.984
Pgp-substrate:	23.246620178222656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.724
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.35
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.258
CYP3A4-inhibitor:	0.682
CYP3A4-substrate:	0.51

ADMET: Excretion

Clearance (CL):	3.718
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.492
Human Hepatotoxicity (H-HT):	0.433
Drug-inuced Liver Injury (DILI):	0.284
AMES Toxicity:	0.158
Rat Oral Acute Toxicity:	0.848
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.427
Carcinogencity:	0.862
Eye Corrosion:	0.004
Eye Irritation:	0.026
Respiratory Toxicity:	0.735

Download Data

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

Natural Product: NPC126556

Natural Product ID:	NPC126556
*Common Name:**	Jerantinine C
IUPAC Name:	n.a.
Synonyms:	Jerantinine C
Standard InCHIKey:	AMYRFECRZHSHRT-FKBYEOEOSA-N
Standard InCHI:	InChI=1S/C22H24N2O5/c1-4-21-6-5-17(26)24-8-7-22(20(21)24)13-9-15(25)16(28-2)10-14(13)23-18(22)12(11-21)19(27)29-3/h5-6,9-10,20,23,25H,4,7-8,11H2,1-3H3/t20-,21-,22-/m0/s1
SMILES:	CC[C@]12C=CC(=O)N3CC[C@@]4(c5cc(c(cc5NC4=C(C1)C(=O)OC)OC)O)[C@H]23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524639
PubChem CID:	25058084
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002672] Plumeran-type alkaloids

*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
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[24773071]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	stem-bark	Pahang, Malaysia	2003-JUN	PMID[25919190]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26918761]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27077800]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29319316]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30869890]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32356659]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	810.0	nM	PMID[475914]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1540.0	nM	PMID[475914]

☑ 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 NPC126556 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	322
0.1-0.2	1628
0.2-0.3	7000
0.3-0.4	10550
0.4-0.5	12818
0.5-0.6	8656
0.6-0.7	1515
0.7-0.8	186
0.8-0.85	10
0.85-0.9	7
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9689	High Similarity	NPC119722
0.9485	High Similarity	NPC269449
0.9326	High Similarity	NPC475147
0.9137	High Similarity	NPC475133
0.902	High Similarity	NPC128476
0.8889	High Similarity	NPC19175
0.8868	High Similarity	NPC291173
0.8705	High Similarity	NPC22476
0.8705	High Similarity	NPC203628
0.8653	High Similarity	NPC5630
0.8557	High Similarity	NPC87714
0.8551	High Similarity	NPC195636
0.8528	High Similarity	NPC303214
0.85	High Similarity	NPC232600
0.8429	Intermediate Similarity	NPC476069
0.8267	Intermediate Similarity	NPC127178
0.8209	Intermediate Similarity	NPC161804
0.8182	Intermediate Similarity	NPC127996
0.8095	Intermediate Similarity	NPC159815
0.8084	Intermediate Similarity	NPC10653
0.8084	Intermediate Similarity	NPC318525
0.8079	Intermediate Similarity	NPC100863
0.8075	Intermediate Similarity	NPC77777
0.8019	Intermediate Similarity	NPC189661
0.7926	Intermediate Similarity	NPC148124
0.7925	Intermediate Similarity	NPC470481
0.7925	Intermediate Similarity	NPC470482
0.788	Intermediate Similarity	NPC99724
0.787	Intermediate Similarity	NPC288110
0.7793	Intermediate Similarity	NPC82541
0.7788	Intermediate Similarity	NPC222046
0.7783	Intermediate Similarity	NPC248903
0.7773	Intermediate Similarity	NPC231924
0.7738	Intermediate Similarity	NPC26928
0.7725	Intermediate Similarity	NPC195787
0.7725	Intermediate Similarity	NPC246140
0.7717	Intermediate Similarity	NPC46259
0.7692	Intermediate Similarity	NPC115588
0.7686	Intermediate Similarity	NPC477395
0.7686	Intermediate Similarity	NPC469722
0.7644	Intermediate Similarity	NPC132874
0.7644	Intermediate Similarity	NPC265642
0.7644	Intermediate Similarity	NPC218733
0.7644	Intermediate Similarity	NPC138615
0.7623	Intermediate Similarity	NPC473458
0.7593	Intermediate Similarity	NPC10732
0.7583	Intermediate Similarity	NPC1464
0.7571	Intermediate Similarity	NPC138830
0.7571	Intermediate Similarity	NPC67904
0.7559	Intermediate Similarity	NPC477161
0.7555	Intermediate Similarity	NPC151171
0.7545	Intermediate Similarity	NPC470480
0.7512	Intermediate Similarity	NPC268077
0.7512	Intermediate Similarity	NPC477186
0.75	Intermediate Similarity	NPC243626
0.7488	Intermediate Similarity	NPC207873
0.7488	Intermediate Similarity	NPC100573
0.7488	Intermediate Similarity	NPC204970
0.7488	Intermediate Similarity	NPC97584
0.7465	Intermediate Similarity	NPC207971
0.7461	Intermediate Similarity	NPC123241
0.7455	Intermediate Similarity	NPC122886
0.7436	Intermediate Similarity	NPC293458
0.7413	Intermediate Similarity	NPC186669
0.7393	Intermediate Similarity	NPC71124
0.7393	Intermediate Similarity	NPC477393
0.7391	Intermediate Similarity	NPC474059
0.7389	Intermediate Similarity	NPC471513
0.7379	Intermediate Similarity	NPC21425
0.7333	Intermediate Similarity	NPC230313
0.7331	Intermediate Similarity	NPC477396
0.7316	Intermediate Similarity	NPC154922
0.7309	Intermediate Similarity	NPC219397
0.7308	Intermediate Similarity	NPC174629
0.7302	Intermediate Similarity	NPC473460
0.7296	Intermediate Similarity	NPC469450
0.7294	Intermediate Similarity	NPC477160
0.7286	Intermediate Similarity	NPC254957
0.7285	Intermediate Similarity	NPC298449
0.7282	Intermediate Similarity	NPC473007
0.7282	Intermediate Similarity	NPC61013
0.7277	Intermediate Similarity	NPC5374
0.7269	Intermediate Similarity	NPC163829
0.7248	Intermediate Similarity	NPC90185
0.7238	Intermediate Similarity	NPC473004
0.7234	Intermediate Similarity	NPC469451
0.7234	Intermediate Similarity	NPC469452
0.7227	Intermediate Similarity	NPC295479
0.7227	Intermediate Similarity	NPC220241
0.7225	Intermediate Similarity	NPC473008
0.7225	Intermediate Similarity	NPC473569
0.7215	Intermediate Similarity	NPC120239
0.7209	Intermediate Similarity	NPC471489
0.7209	Intermediate Similarity	NPC469732
0.7208	Intermediate Similarity	NPC248117
0.7202	Intermediate Similarity	NPC478075
0.7198	Intermediate Similarity	NPC476220
0.7198	Intermediate Similarity	NPC160113
0.7188	Intermediate Similarity	NPC303658
0.7179	Intermediate Similarity	NPC301501
0.7175	Intermediate Similarity	NPC234772
0.7174	Intermediate Similarity	NPC477397
0.7174	Intermediate Similarity	NPC223242
0.7173	Intermediate Similarity	NPC329932
0.7171	Intermediate Similarity	NPC283810
0.7171	Intermediate Similarity	NPC85613
0.7171	Intermediate Similarity	NPC5167
0.7161	Intermediate Similarity	NPC113455
0.7157	Intermediate Similarity	NPC193410
0.7157	Intermediate Similarity	NPC36495
0.715	Intermediate Similarity	NPC17677
0.7137	Intermediate Similarity	NPC131977
0.713	Intermediate Similarity	NPC194740
0.7123	Intermediate Similarity	NPC16249
0.7122	Intermediate Similarity	NPC99043
0.7122	Intermediate Similarity	NPC218594
0.7115	Intermediate Similarity	NPC102760
0.7112	Intermediate Similarity	NPC139373
0.711	Intermediate Similarity	NPC14339
0.7108	Intermediate Similarity	NPC264482
0.7108	Intermediate Similarity	NPC203202
0.7107	Intermediate Similarity	NPC329982
0.7095	Intermediate Similarity	NPC162694
0.7087	Intermediate Similarity	NPC39822
0.7078	Intermediate Similarity	NPC303374
0.7078	Intermediate Similarity	NPC158551
0.7076	Intermediate Similarity	NPC304837
0.7076	Intermediate Similarity	NPC476258
0.7067	Intermediate Similarity	NPC313327
0.7056	Intermediate Similarity	NPC97100
0.7056	Intermediate Similarity	NPC311906
0.7056	Intermediate Similarity	NPC473375
0.7044	Intermediate Similarity	NPC471604
0.7043	Intermediate Similarity	NPC476436
0.7042	Intermediate Similarity	NPC203972
0.7039	Intermediate Similarity	NPC287152
0.7035	Intermediate Similarity	NPC182853
0.7032	Intermediate Similarity	NPC470484
0.703	Intermediate Similarity	NPC224970
0.703	Intermediate Similarity	NPC167724
0.703	Intermediate Similarity	NPC223595
0.703	Intermediate Similarity	NPC33507
0.7023	Intermediate Similarity	NPC24228
0.7019	Intermediate Similarity	NPC159963
0.7014	Intermediate Similarity	NPC230098
0.7004	Intermediate Similarity	NPC475816
0.7	Intermediate Similarity	NPC469734
0.6992	Remote Similarity	NPC184680
0.698	Remote Similarity	NPC476569
0.6978	Remote Similarity	NPC55470
0.6977	Remote Similarity	NPC33256
0.6968	Remote Similarity	NPC222561
0.6968	Remote Similarity	NPC308943
0.6967	Remote Similarity	NPC14994
0.6964	Remote Similarity	NPC89549
0.6963	Remote Similarity	NPC94499
0.6963	Remote Similarity	NPC470485
0.6962	Remote Similarity	NPC470785
0.6962	Remote Similarity	NPC470784
0.6957	Remote Similarity	NPC6974
0.6952	Remote Similarity	NPC52262
0.6948	Remote Similarity	NPC28510
0.6948	Remote Similarity	NPC25401
0.6943	Remote Similarity	NPC118189
0.6938	Remote Similarity	NPC474745
0.6927	Remote Similarity	NPC477185
0.6926	Remote Similarity	NPC477394
0.6919	Remote Similarity	NPC33902
0.6919	Remote Similarity	NPC276674
0.6916	Remote Similarity	NPC305984
0.6913	Remote Similarity	NPC71539
0.6913	Remote Similarity	NPC250960
0.6912	Remote Similarity	NPC293624
0.6908	Remote Similarity	NPC477187
0.6906	Remote Similarity	NPC471561
0.6905	Remote Similarity	NPC298339
0.69	Remote Similarity	NPC147091
0.6899	Remote Similarity	NPC260909
0.6898	Remote Similarity	NPC125924
0.6897	Remote Similarity	NPC279527
0.6897	Remote Similarity	NPC214960
0.6894	Remote Similarity	NPC476429
0.689	Remote Similarity	NPC474325
0.6886	Remote Similarity	NPC473041
0.6886	Remote Similarity	NPC96321
0.6878	Remote Similarity	NPC473422
0.687	Remote Similarity	NPC76478
0.6869	Remote Similarity	NPC470483
0.6864	Remote Similarity	NPC473005
0.6861	Remote Similarity	NPC205926
0.6858	Remote Similarity	NPC473006
0.6854	Remote Similarity	NPC320088
0.6852	Remote Similarity	NPC221687
0.6852	Remote Similarity	NPC469816
0.6852	Remote Similarity	NPC469815
0.6849	Remote Similarity	NPC25897
0.6847	Remote Similarity	NPC299582
0.6847	Remote Similarity	NPC70172
0.6845	Remote Similarity	NPC470324
0.6842	Remote Similarity	NPC70092

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 NPC126556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	586
0.2-0.3	861
0.3-0.4	1876
0.4-0.5	2867
0.5-0.6	2302
0.6-0.7	448
0.7-0.8	22
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7751	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD4859	Phase 1
0.7571	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD683	Approved
0.7311	Intermediate Similarity	NPD5071	Phase 2
0.7252	Intermediate Similarity	NPD8149	Discontinued
0.7227	Intermediate Similarity	NPD4493	Discontinued
0.7217	Intermediate Similarity	NPD5582	Discontinued
0.7212	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6723	Discontinued
0.715	Intermediate Similarity	NPD7281	Phase 3
0.715	Intermediate Similarity	NPD7280	Phase 3
0.7149	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7559	Phase 2
0.7118	Intermediate Similarity	NPD7186	Phase 3
0.7091	Intermediate Similarity	NPD4082	Approved
0.7087	Intermediate Similarity	NPD6297	Approved
0.7085	Intermediate Similarity	NPD4455	Discontinued
0.7079	Intermediate Similarity	NPD5186	Approved
0.7079	Intermediate Similarity	NPD5183	Approved
0.7048	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4596	Phase 1
0.7045	Intermediate Similarity	NPD7263	Phase 2
0.704	Intermediate Similarity	NPD4494	Approved
0.704	Intermediate Similarity	NPD4492	Approved
0.704	Intermediate Similarity	NPD3888	Discontinued
0.7039	Intermediate Similarity	NPD7479	Phase 2
0.7027	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3893	Discontinued
0.7018	Intermediate Similarity	NPD6795	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3793	Phase 3
0.699	Remote Similarity	NPD5600	Discontinued
0.6966	Remote Similarity	NPD4885	Approved
0.6963	Remote Similarity	NPD3631	Phase 3
0.6955	Remote Similarity	NPD3298	Approved
0.6952	Remote Similarity	NPD6853	Approved
0.6952	Remote Similarity	NPD6851	Approved
0.6948	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3472	Approved
0.6937	Remote Similarity	NPD4022	Approved
0.693	Remote Similarity	NPD2899	Discontinued
0.6916	Remote Similarity	NPD5937	Approved
0.6912	Remote Similarity	NPD4668	Phase 2
0.6908	Remote Similarity	NPD5312	Approved
0.6908	Remote Similarity	NPD5313	Approved
0.6906	Remote Similarity	NPD3592	Approved
0.6906	Remote Similarity	NPD3591	Approved
0.6905	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5928	Phase 1
0.69	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD8459	Approved
0.6899	Remote Similarity	NPD8460	Approved
0.6895	Remote Similarity	NPD6238	Discontinued
0.6889	Remote Similarity	NPD7225	Discontinued
0.6881	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3372	Discontinued
0.6872	Remote Similarity	NPD5025	Approved
0.6863	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6457	Approved
0.6863	Remote Similarity	NPD3983	Phase 3
0.6854	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4796	Discontinued
0.6845	Remote Similarity	NPD2898	Approved
0.6838	Remote Similarity	NPD8363	Approved
0.6838	Remote Similarity	NPD8364	Approved
0.6837	Remote Similarity	NPD3634	Approved
0.6837	Remote Similarity	NPD3633	Approved
0.6832	Remote Similarity	NPD1743	Approved
0.6832	Remote Similarity	NPD1742	Approved
0.6832	Remote Similarity	NPD19	Approved
0.6829	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3437	Discontinued
0.6822	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD8091	Phase 3
0.6809	Remote Similarity	NPD8466	Approved
0.6809	Remote Similarity	NPD8429	Approved
0.6809	Remote Similarity	NPD8428	Approved
0.6809	Remote Similarity	NPD8427	Approved
0.6809	Remote Similarity	NPD8465	Approved
0.6809	Remote Similarity	NPD8467	Approved
0.68	Remote Similarity	NPD5860	Discontinued
0.6794	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6625	Approved
0.6792	Remote Similarity	NPD7560	Approved
0.6787	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD824	Approved
0.6784	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5496	Approved
0.678	Remote Similarity	NPD2821	Approved
0.6767	Remote Similarity	NPD6997	Phase 2
0.6762	Remote Similarity	NPD5445	Approved
0.6748	Remote Similarity	NPD4166	Phase 2
0.6746	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3912	Discontinued
0.6737	Remote Similarity	NPD6199	Discontinued
0.6737	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6517	Phase 3
0.6728	Remote Similarity	NPD4539	Phase 1
0.6728	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5610	Approved
0.6727	Remote Similarity	NPD3297	Approved
0.6715	Remote Similarity	NPD4083	Discontinued
0.6714	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5658	Approved
0.6709	Remote Similarity	NPD3442	Approved
0.6709	Remote Similarity	NPD3441	Approved
0.6705	Remote Similarity	NPD8426	Approved
0.6705	Remote Similarity	NPD8425	Approved
0.6696	Remote Similarity	NPD1945	Phase 1
0.6683	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4897	Phase 2
0.6667	Remote Similarity	NPD4981	Phase 2
0.6667	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7827	Phase 1
0.6653	Remote Similarity	NPD7955	Approved
0.6653	Remote Similarity	NPD7956	Approved
0.6652	Remote Similarity	NPD4467	Phase 2
0.6652	Remote Similarity	NPD4465	Phase 2
0.6651	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD2906	Approved
0.6637	Remote Similarity	NPD2907	Approved
0.6636	Remote Similarity	NPD6618	Phase 2
0.6622	Remote Similarity	NPD6612	Phase 2
0.662	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3349	Phase 2
0.6611	Remote Similarity	NPD7797	Approved
0.6611	Remote Similarity	NPD7796	Approved
0.6607	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6877	Discontinued
0.66	Remote Similarity	NPD1670	Discontinued
0.6592	Remote Similarity	NPD3416	Discontinued
0.6591	Remote Similarity	NPD3964	Approved
0.659	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4373	Phase 2
0.658	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4040	Phase 1
0.6571	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.657	Remote Similarity	NPD4846	Phase 2
0.657	Remote Similarity	NPD6982	Phase 2
0.6562	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.656	Remote Similarity	NPD2490	Approved
0.656	Remote Similarity	NPD2488	Approved
0.656	Remote Similarity	NPD5641	Discontinued
0.656	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2672	Discontinued
0.655	Remote Similarity	NPD4206	Approved
0.6545	Remote Similarity	NPD7669	Phase 3
0.6544	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6107	Approved
0.6528	Remote Similarity	NPD6340	Approved
0.6528	Remote Similarity	NPD6339	Approved
0.6523	Remote Similarity	NPD7803	Approved
0.6522	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD2845	Phase 2
0.6514	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD2843	Phase 2
0.6512	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD5507	Approved
0.6511	Remote Similarity	NPD5506	Approved
0.6511	Remote Similarity	NPD7805	Phase 3
0.6509	Remote Similarity	NPD5562	Approved
0.6509	Remote Similarity	NPD7047	Phase 3
0.6509	Remote Similarity	NPD5561	Approved
0.6504	Remote Similarity	NPD7891	Discontinued
0.6502	Remote Similarity	NPD6874	Approved
0.6502	Remote Similarity	NPD7048	Phase 3
0.6496	Remote Similarity	NPD3258	Approved
0.6492	Remote Similarity	NPD8358	Approved
0.6491	Remote Similarity	NPD8027	Approved
0.6486	Remote Similarity	NPD5515	Phase 2
0.6482	Remote Similarity	NPD3141	Discontinued
0.6482	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5457	Discontinued
0.6471	Remote Similarity	NPD7256	Discontinued
0.6468	Remote Similarity	NPD7291	Discontinued
0.6465	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD2680	Approved
0.6459	Remote Similarity	NPD2681	Approved
0.6458	Remote Similarity	NPD4952	Phase 3
0.6456	Remote Similarity	NPD7278	Phase 2
0.6456	Remote Similarity	NPD7279	Phase 2
0.6449	Remote Similarity	NPD8016	Phase 3
0.6449	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7922	Phase 1
0.6445	Remote Similarity	NPD2246	Approved
0.6445	Remote Similarity	NPD2248	Approved
0.6444	Remote Similarity	NPD7476	Discontinued
0.6444	Remote Similarity	NPD4328	Approved
0.6441	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD3639	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