NPASS Compound

Structure

NPC475133 OpenBabel07101719252D 31 35 0 0 1 0 0 0 0 0999 V2000 2.5370 -1.8762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9856 1.3107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8922 -1.9916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3611 -5.1266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5853 -2.1834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 -1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5461 -0.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8734 0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9463 0.3232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1725 -0.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9856 -1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5692 -2.2783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9856 1.3107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2003 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7659 -1.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1725 -1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3922 -1.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9856 -0.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8855 -2.1033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3197 -3.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8435 -1.5128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9705 -1.2946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6284 -2.4341 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -3.4856 2.1767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2392 -3.9269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3922 -1.1256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4804 -4.1337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4856 0.4446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 14 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 7 23 1 0 0 0 0 8 10 1 0 0 0 0 9 26 1 0 0 0 0 10 26 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 27 2 0 0 0 0 14 31 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 19 2 0 0 0 0 18 29 1 0 0 0 0 19 31 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 28 2 0 0 0 0 21 30 1 0 0 0 0 22 23 1 1 0 0 0 22 24 1 0 0 0 0 22 26 1 0 0 0 0 23 5 1 6 0 0 0 24 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.2
Volume:	428.367
LogP:	1.93
LogD:	1.715
LogS:	-3.487
# Rotatable Bonds:	6
TPSA:	77.43
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	5.027
Fsp3:	0.542
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.869
MDCK Permeability:	2.7712310838978738e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.153
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.103
30% Bioavailability (F30%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.919
Plasma Protein Binding (PPB):	50.44029235839844%
Volume Distribution (VD):	1.038
Pgp-substrate:	59.298919677734375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.08
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.481
CYP2D6-inhibitor:	0.644
CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.777

ADMET: Excretion

Clearance (CL):	4.058
Half-life (T1/2):	0.429

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.18
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.729
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.37
Carcinogencity:	0.761
Eye Corrosion:	0.006
Eye Irritation:	0.077
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC475133

Natural Product ID:	NPC475133
*Common Name:**	Jerantinine A Acetate
IUPAC Name:	n.a.
Synonyms:	Jerantinine A Acetate
Standard InCHIKey:	IMCYDSFSAPKANT-HJOGWXRNSA-N
Standard InCHI:	InChI=1S/C24H28N2O5/c1-5-23-7-6-9-26-10-8-24(22(23)26)16-11-19(31-14(2)27)18(29-3)12-17(16)25-20(24)15(13-23)21(28)30-4/h6-7,11-12,22,25H,5,8-10,13H2,1-4H3/t22-,23-,24-/m0/s1
SMILES:	COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@@](C1)(CC)C=CCN2CC4)cc(c(c3)OC)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499064
PubChem CID:	25058087
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.	leaf	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	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	=	1040.0	nM	PMID[537666]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	830.0	nM	PMID[537666]

☑ 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 NPC475133 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	346
0.1-0.2	1749
0.2-0.3	7309
0.3-0.4	10207
0.4-0.5	13294
0.5-0.6	8111
0.6-0.7	1446
0.7-0.8	213
0.8-0.85	11
0.85-0.9	5
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9784	High Similarity	NPC475147
0.9427	High Similarity	NPC119722
0.9137	High Similarity	NPC126556
0.9135	High Similarity	NPC22476
0.9124	High Similarity	NPC269449
0.9095	High Similarity	NPC476069
0.8945	High Similarity	NPC195636
0.8768	High Similarity	NPC128476
0.8673	High Similarity	NPC87714
0.8641	High Similarity	NPC19175
0.8632	High Similarity	NPC203628
0.8579	High Similarity	NPC5630
0.8454	Intermediate Similarity	NPC303214
0.8426	Intermediate Similarity	NPC232600
0.8284	Intermediate Similarity	NPC127996
0.8279	Intermediate Similarity	NPC291173
0.8199	Intermediate Similarity	NPC231924
0.8195	Intermediate Similarity	NPC159815
0.8173	Intermediate Similarity	NPC77777
0.8116	Intermediate Similarity	NPC189661
0.801	Intermediate Similarity	NPC127178
0.8	Intermediate Similarity	NPC100863
0.7944	Intermediate Similarity	NPC115588
0.7928	Intermediate Similarity	NPC469722
0.7925	Intermediate Similarity	NPC10653
0.7925	Intermediate Similarity	NPC318525
0.7885	Intermediate Similarity	NPC82541
0.7865	Intermediate Similarity	NPC186669
0.7838	Intermediate Similarity	NPC123241
0.7816	Intermediate Similarity	NPC195787
0.7816	Intermediate Similarity	NPC246140
0.7807	Intermediate Similarity	NPC293458
0.7727	Intermediate Similarity	NPC21425
0.771	Intermediate Similarity	NPC288110
0.7678	Intermediate Similarity	NPC10732
0.7673	Intermediate Similarity	NPC243626
0.7659	Intermediate Similarity	NPC138830
0.7659	Intermediate Similarity	NPC67904
0.7647	Intermediate Similarity	NPC61013
0.7644	Intermediate Similarity	NPC477161
0.7628	Intermediate Similarity	NPC222046
0.7623	Intermediate Similarity	NPC154922
0.7576	Intermediate Similarity	NPC97584
0.7566	Intermediate Similarity	NPC248117
0.7561	Intermediate Similarity	NPC138615
0.7561	Intermediate Similarity	NPC132874
0.7561	Intermediate Similarity	NPC265642
0.7561	Intermediate Similarity	NPC218733
0.7558	Intermediate Similarity	NPC46259
0.7557	Intermediate Similarity	NPC223242
0.7556	Intermediate Similarity	NPC151171
0.7523	Intermediate Similarity	NPC148124
0.7513	Intermediate Similarity	NPC193410
0.7512	Intermediate Similarity	NPC161804
0.7512	Intermediate Similarity	NPC268077
0.7511	Intermediate Similarity	NPC120239
0.7511	Intermediate Similarity	NPC131977
0.75	Intermediate Similarity	NPC1464
0.75	Intermediate Similarity	NPC160113
0.75	Intermediate Similarity	NPC476220
0.75	Intermediate Similarity	NPC230313
0.7489	Intermediate Similarity	NPC139373
0.7477	Intermediate Similarity	NPC99724
0.7475	Intermediate Similarity	NPC474059
0.7466	Intermediate Similarity	NPC473458
0.7464	Intermediate Similarity	NPC207971
0.7456	Intermediate Similarity	NPC113455
0.7449	Intermediate Similarity	NPC264482
0.7449	Intermediate Similarity	NPC203202
0.7445	Intermediate Similarity	NPC469450
0.7437	Intermediate Similarity	NPC159963
0.7424	Intermediate Similarity	NPC5167
0.7424	Intermediate Similarity	NPC85613
0.7424	Intermediate Similarity	NPC283810
0.7387	Intermediate Similarity	NPC248903
0.738	Intermediate Similarity	NPC469451
0.738	Intermediate Similarity	NPC469452
0.7376	Intermediate Similarity	NPC14994
0.7371	Intermediate Similarity	NPC223595
0.7371	Intermediate Similarity	NPC167724
0.7371	Intermediate Similarity	NPC224970
0.7368	Intermediate Similarity	NPC476258
0.7368	Intermediate Similarity	NPC304837
0.7363	Intermediate Similarity	NPC473007
0.7353	Intermediate Similarity	NPC25401
0.7342	Intermediate Similarity	NPC476436
0.7342	Intermediate Similarity	NPC26928
0.7327	Intermediate Similarity	NPC234772
0.7325	Intermediate Similarity	NPC301501
0.7317	Intermediate Similarity	NPC473004
0.7316	Intermediate Similarity	NPC329932
0.7308	Intermediate Similarity	NPC71124
0.7304	Intermediate Similarity	NPC473008
0.7304	Intermediate Similarity	NPC477395
0.7304	Intermediate Similarity	NPC473569
0.7299	Intermediate Similarity	NPC473460
0.7296	Intermediate Similarity	NPC471604
0.7286	Intermediate Similarity	NPC6974
0.7269	Intermediate Similarity	NPC470482
0.7269	Intermediate Similarity	NPC470481
0.7255	Intermediate Similarity	NPC477186
0.7241	Intermediate Similarity	NPC477393
0.7233	Intermediate Similarity	NPC204970
0.7232	Intermediate Similarity	NPC471513
0.7231	Intermediate Similarity	NPC476569
0.7215	Intermediate Similarity	NPC313327
0.72	Intermediate Similarity	NPC99043
0.72	Intermediate Similarity	NPC218594
0.7198	Intermediate Similarity	NPC254957
0.7196	Intermediate Similarity	NPC478075
0.719	Intermediate Similarity	NPC5374
0.7182	Intermediate Similarity	NPC96321
0.7182	Intermediate Similarity	NPC473041
0.7181	Intermediate Similarity	NPC476429
0.7179	Intermediate Similarity	NPC477396
0.7173	Intermediate Similarity	NPC329982
0.715	Intermediate Similarity	NPC36495
0.7149	Intermediate Similarity	NPC219397
0.7143	Intermediate Similarity	NPC23080
0.7143	Intermediate Similarity	NPC193906
0.7136	Intermediate Similarity	NPC329338
0.7136	Intermediate Similarity	NPC474708
0.7136	Intermediate Similarity	NPC469726
0.713	Intermediate Similarity	NPC477160
0.7123	Intermediate Similarity	NPC469732
0.7108	Intermediate Similarity	NPC102760
0.7108	Intermediate Similarity	NPC52262
0.7093	Intermediate Similarity	NPC477397
0.7092	Intermediate Similarity	NPC24954
0.7092	Intermediate Similarity	NPC299582
0.7092	Intermediate Similarity	NPC70172
0.7085	Intermediate Similarity	NPC475845
0.7079	Intermediate Similarity	NPC35680
0.7079	Intermediate Similarity	NPC70092
0.7067	Intermediate Similarity	NPC122886
0.7065	Intermediate Similarity	NPC4669
0.7048	Intermediate Similarity	NPC311906
0.704	Intermediate Similarity	NPC472099
0.7035	Intermediate Similarity	NPC474324
0.7035	Intermediate Similarity	NPC57812
0.7033	Intermediate Similarity	NPC203972
0.7026	Intermediate Similarity	NPC93653
0.7005	Intermediate Similarity	NPC230098
0.7004	Intermediate Similarity	NPC470480
0.7	Intermediate Similarity	NPC303374
0.699	Remote Similarity	NPC230942
0.699	Remote Similarity	NPC282339
0.699	Remote Similarity	NPC99632
0.699	Remote Similarity	NPC315498
0.6986	Remote Similarity	NPC63152
0.6971	Remote Similarity	NPC141440
0.6971	Remote Similarity	NPC174629
0.6967	Remote Similarity	NPC477258
0.6959	Remote Similarity	NPC222561
0.6955	Remote Similarity	NPC472098
0.6951	Remote Similarity	NPC195120
0.6951	Remote Similarity	NPC87560
0.6951	Remote Similarity	NPC303658
0.6946	Remote Similarity	NPC287152
0.6944	Remote Similarity	NPC14339
0.6937	Remote Similarity	NPC152768
0.6937	Remote Similarity	NPC148183
0.6934	Remote Similarity	NPC272706
0.693	Remote Similarity	NPC473005
0.6927	Remote Similarity	NPC474745
0.6927	Remote Similarity	NPC149285
0.6923	Remote Similarity	NPC473006
0.6923	Remote Similarity	NPC78733
0.692	Remote Similarity	NPC469734
0.6916	Remote Similarity	NPC21638
0.6914	Remote Similarity	NPC284685
0.6912	Remote Similarity	NPC287588
0.6912	Remote Similarity	NPC474470
0.6909	Remote Similarity	NPC295479
0.6909	Remote Similarity	NPC220241
0.6906	Remote Similarity	NPC305984
0.6901	Remote Similarity	NPC17677
0.69	Remote Similarity	NPC194740
0.6898	Remote Similarity	NPC41216
0.6897	Remote Similarity	NPC127082
0.6897	Remote Similarity	NPC285941
0.6895	Remote Similarity	NPC168250
0.6895	Remote Similarity	NPC471561
0.6893	Remote Similarity	NPC179704
0.6892	Remote Similarity	NPC55470
0.6888	Remote Similarity	NPC57512
0.6887	Remote Similarity	NPC473375
0.6887	Remote Similarity	NPC33256
0.6887	Remote Similarity	NPC97100
0.6887	Remote Similarity	NPC125924
0.6884	Remote Similarity	NPC295676
0.6884	Remote Similarity	NPC471489
0.6883	Remote Similarity	NPC475720
0.6883	Remote Similarity	NPC474192
0.6881	Remote Similarity	NPC308943
0.6878	Remote Similarity	NPC81939
0.6878	Remote Similarity	NPC474325
0.6878	Remote Similarity	NPC288305
0.6875	Remote Similarity	NPC214629
0.6872	Remote Similarity	NPC302001

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 NPC475133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	623
0.2-0.3	885
0.3-0.4	1757
0.4-0.5	2922
0.5-0.6	2206
0.6-0.7	538
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
0.7913	Intermediate Similarity	NPD4859	Phase 1
0.7585	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD683	Approved
0.7301	Intermediate Similarity	NPD6625	Approved
0.7282	Intermediate Similarity	NPD6457	Approved
0.7281	Intermediate Similarity	NPD7559	Phase 2
0.726	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5071	Phase 2
0.715	Intermediate Similarity	NPD5600	Discontinued
0.7122	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD3297	Approved
0.7085	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5183	Approved
0.7071	Intermediate Similarity	NPD5186	Approved
0.7064	Intermediate Similarity	NPD4493	Discontinued
0.7059	Intermediate Similarity	NPD3940	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6046	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD3298	Approved
0.702	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3983	Phase 3
0.7005	Intermediate Similarity	NPD5658	Approved
0.7005	Intermediate Similarity	NPD4796	Discontinued
0.7	Intermediate Similarity	NPD6723	Discontinued
0.699	Remote Similarity	NPD1742	Approved
0.699	Remote Similarity	NPD19	Approved
0.699	Remote Similarity	NPD1743	Approved
0.698	Remote Similarity	NPD5312	Approved
0.698	Remote Similarity	NPD5313	Approved
0.6974	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5582	Discontinued
0.6964	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6238	Discontinued
0.696	Remote Similarity	NPD7186	Phase 3
0.6957	Remote Similarity	NPD4885	Approved
0.6946	Remote Similarity	NPD7479	Phase 2
0.6946	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8149	Discontinued
0.6935	Remote Similarity	NPD2680	Approved
0.6935	Remote Similarity	NPD6107	Approved
0.6935	Remote Similarity	NPD2681	Approved
0.6927	Remote Similarity	NPD4082	Approved
0.6923	Remote Similarity	NPD4455	Discontinued
0.6923	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4481	Phase 3
0.6915	Remote Similarity	NPD2248	Approved
0.6915	Remote Similarity	NPD2246	Approved
0.6914	Remote Similarity	NPD7956	Approved
0.6914	Remote Similarity	NPD7955	Approved
0.6901	Remote Similarity	NPD6877	Discontinued
0.6897	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3591	Approved
0.6895	Remote Similarity	NPD3592	Approved
0.6893	Remote Similarity	NPD7281	Phase 3
0.6893	Remote Similarity	NPD7280	Phase 3
0.689	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3964	Approved
0.6881	Remote Similarity	NPD4596	Phase 1
0.6878	Remote Similarity	NPD4492	Approved
0.6878	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4494	Approved
0.6878	Remote Similarity	NPD3888	Discontinued
0.6872	Remote Similarity	NPD7278	Phase 2
0.6872	Remote Similarity	NPD7279	Phase 2
0.6872	Remote Similarity	NPD3631	Phase 3
0.687	Remote Similarity	NPD6199	Discontinued
0.6869	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD8429	Approved
0.6865	Remote Similarity	NPD8428	Approved
0.6865	Remote Similarity	NPD8427	Approved
0.6865	Remote Similarity	NPD8467	Approved
0.6865	Remote Similarity	NPD8466	Approved
0.6865	Remote Similarity	NPD8465	Approved
0.6864	Remote Similarity	NPD3893	Discontinued
0.6861	Remote Similarity	NPD5025	Approved
0.6857	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3511	Discontinued
0.6842	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.684	Remote Similarity	NPD3442	Approved
0.684	Remote Similarity	NPD3441	Approved
0.684	Remote Similarity	NPD4418	Discontinued
0.6839	Remote Similarity	NPD6031	Approved
0.6839	Remote Similarity	NPD6030	Approved
0.6837	Remote Similarity	NPD3289	Phase 3
0.6837	Remote Similarity	NPD3290	Approved
0.6835	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6297	Approved
0.6827	Remote Similarity	NPD8363	Approved
0.6827	Remote Similarity	NPD8364	Approved
0.6825	Remote Similarity	NPD3634	Approved
0.6825	Remote Similarity	NPD3633	Approved
0.6814	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5928	Phase 1
0.681	Remote Similarity	NPD2845	Phase 2
0.681	Remote Similarity	NPD2843	Phase 2
0.6806	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7225	Discontinued
0.6798	Remote Similarity	NPD3912	Discontinued
0.6797	Remote Similarity	NPD4952	Phase 3
0.6789	Remote Similarity	NPD7891	Discontinued
0.6788	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6851	Approved
0.6779	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6853	Approved
0.6776	Remote Similarity	NPD5515	Phase 2
0.6774	Remote Similarity	NPD7803	Approved
0.6773	Remote Similarity	NPD4022	Approved
0.6773	Remote Similarity	NPD3472	Approved
0.6773	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4356	Discontinued
0.6761	Remote Similarity	NPD7256	Discontinued
0.6759	Remote Similarity	NPD4107	Approved
0.6758	Remote Similarity	NPD8459	Approved
0.6758	Remote Similarity	NPD8425	Approved
0.6758	Remote Similarity	NPD8426	Approved
0.6758	Remote Similarity	NPD8460	Approved
0.6757	Remote Similarity	NPD1945	Phase 1
0.6753	Remote Similarity	NPD3639	Approved
0.6753	Remote Similarity	NPD3640	Phase 3
0.6753	Remote Similarity	NPD3641	Approved
0.675	Remote Similarity	NPD8358	Approved
0.6746	Remote Similarity	NPD6339	Approved
0.6746	Remote Similarity	NPD6340	Approved
0.6745	Remote Similarity	NPD5937	Approved
0.6744	Remote Similarity	NPD4420	Approved
0.6744	Remote Similarity	NPD4668	Phase 2
0.6733	Remote Similarity	NPD4166	Phase 2
0.6731	Remote Similarity	NPD2968	Approved
0.6731	Remote Similarity	NPD2971	Approved
0.673	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7476	Discontinued
0.6728	Remote Similarity	NPD4482	Phase 3
0.6726	Remote Similarity	NPD5632	Approved
0.6724	Remote Similarity	NPD4981	Phase 2
0.6716	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5860	Discontinued
0.6712	Remote Similarity	NPD3372	Discontinued
0.6712	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5561	Approved
0.6711	Remote Similarity	NPD5562	Approved
0.6709	Remote Similarity	NPD4373	Phase 2
0.6709	Remote Similarity	NPD7560	Approved
0.67	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4083	Discontinued
0.6697	Remote Similarity	NPD5006	Approved
0.6697	Remote Similarity	NPD4154	Approved
0.6697	Remote Similarity	NPD2907	Approved
0.6697	Remote Similarity	NPD2906	Approved
0.6697	Remote Similarity	NPD8027	Approved
0.6697	Remote Similarity	NPD7627	Approved
0.6697	Remote Similarity	NPD5005	Approved
0.6697	Remote Similarity	NPD7626	Approved
0.6697	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5496	Approved
0.6695	Remote Similarity	NPD4846	Phase 2
0.6684	Remote Similarity	NPD2653	Approved
0.6683	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2821	Approved
0.668	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1769	Discontinued
0.6667	Remote Similarity	NPD3437	Discontinued
0.6667	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.665	Remote Similarity	NPD3793	Phase 3
0.665	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7528	Approved
0.6636	Remote Similarity	NPD6874	Approved
0.6635	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3516	Approved
0.6621	Remote Similarity	NPD3515	Approved
0.6616	Remote Similarity	NPD6873	Phase 2
0.6613	Remote Similarity	NPD6228	Discontinued
0.6613	Remote Similarity	NPD7708	Approved
0.661	Remote Similarity	NPD6964	Approved
0.661	Remote Similarity	NPD6963	Approved
0.6609	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5457	Discontinued
0.6604	Remote Similarity	NPD7291	Discontinued
0.6604	Remote Similarity	NPD3349	Phase 2
0.6604	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6357	Discontinued
0.6597	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD5866	Approved
0.6578	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7263	Phase 2
0.6571	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6644	Discontinued
0.6561	Remote Similarity	NPD4040	Phase 1
0.656	Remote Similarity	NPD1880	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