NPASS Compound

Structure

CID19175 OpenBabel06191715342D 29 34 0 0 1 0 0 0 0 0999 V2000 1.9380 2.5237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5720 2.3681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0254 5.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6897 1.7918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3324 0.7688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9455 -0.0996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0960 0.9298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0961 2.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0203 2.3562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7108 -0.3036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1973 2.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2725 1.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2726 2.3560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9190 1.4050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9190 2.3559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3913 0.0629 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6261 2.3561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5291 0.8234 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1974 3.7817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1974 0.9300 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0204 1.4053 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6261 1.4052 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4496 2.8313 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 -4.7219 0.9414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1425 3.8810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7421 2.8310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3612 4.5506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1188 0.3238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 5 6 1 0 0 0 0 6 24 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 11 1 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 25 1 0 0 0 0 15 27 1 0 0 0 0 16 10 1 1 0 0 0 16 18 1 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 1 0 0 0 18 29 1 0 0 0 0 19 26 2 0 0 0 0 19 28 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 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.18
Volume:	390.492
LogP:	1.706
LogD:	1.884
LogS:	-3.504
# Rotatable Bonds:	4
TPSA:	83.89
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	5.409
Fsp3:	0.636
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:	-5.316
MDCK Permeability:	1.541513302072417e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	72.89237213134766%
Volume Distribution (VD):	1.767
Pgp-substrate:	39.74213790893555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.318
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.809
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.778

ADMET: Excretion

Clearance (CL):	10.188
Half-life (T1/2):	0.558

ADMET: Toxicity

hERG Blockers:	0.672
Human Hepatotoxicity (H-HT):	0.527
Drug-inuced Liver Injury (DILI):	0.379
AMES Toxicity:	0.169
Rat Oral Acute Toxicity:	0.476
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.182
Carcinogencity:	0.834
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC19175

Natural Product ID:	NPC19175
*Common Name:**	Jerantinine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BECBFSXLBJGONE-DIMUUIPOSA-N
Standard InCHI:	InChI=1S/C22H26N2O5/c1-4-21-9-11(19(26)28-3)17-22(5-6-24(20(21)22)10-16-18(21)29-16)12-7-14(25)15(27-2)8-13(12)23-17/h7-8,16,18,20,23,25H,4-6,9-10H2,1-3H3/t16-,18-,20-,21+,22-/m0/s1
SMILES:	COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@@](C1)(CC)[C@H]1O[C@H]1CN2CC4)cc(c(c3)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446954
PubChem CID:	25058083
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002755] Aspidospermatan-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	=	1110.0	nM	PMID[568636]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	950.0	nM	PMID[568636]

☑ 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 NPC19175 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	331
0.1-0.2	1568
0.2-0.3	4879
0.3-0.4	12125
0.4-0.5	9719
0.5-0.6	12344
0.6-0.7	1517
0.7-0.8	176
0.8-0.85	26
0.85-0.9	6
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9652	High Similarity	NPC128476
0.9648	High Similarity	NPC195636
0.9567	High Similarity	NPC291173
0.9505	High Similarity	NPC476069
0.9347	High Similarity	NPC269449
0.9064	High Similarity	NPC119722
0.8889	High Similarity	NPC126556
0.8719	High Similarity	NPC475147
0.8667	High Similarity	NPC77777
0.8641	High Similarity	NPC475133
0.8627	High Similarity	NPC87714
0.8436	Intermediate Similarity	NPC189661
0.8426	Intermediate Similarity	NPC231924
0.8406	Intermediate Similarity	NPC195787
0.8406	Intermediate Similarity	NPC246140
0.8393	Intermediate Similarity	NPC477395
0.823	Intermediate Similarity	NPC469722
0.8173	Intermediate Similarity	NPC1464
0.8157	Intermediate Similarity	NPC318525
0.8157	Intermediate Similarity	NPC10653
0.8128	Intermediate Similarity	NPC22476
0.8128	Intermediate Similarity	NPC203628
0.8084	Intermediate Similarity	NPC127996
0.8079	Intermediate Similarity	NPC5630
0.8079	Intermediate Similarity	NPC477393
0.8038	Intermediate Similarity	NPC232600
0.8018	Intermediate Similarity	NPC473458
0.8009	Intermediate Similarity	NPC477396
0.7982	Intermediate Similarity	NPC469450
0.7971	Intermediate Similarity	NPC303214
0.796	Intermediate Similarity	NPC159963
0.7919	Intermediate Similarity	NPC148124
0.7917	Intermediate Similarity	NPC159815
0.7913	Intermediate Similarity	NPC469451
0.7913	Intermediate Similarity	NPC469452
0.7892	Intermediate Similarity	NPC14994
0.7873	Intermediate Similarity	NPC99724
0.7867	Intermediate Similarity	NPC223242
0.7867	Intermediate Similarity	NPC477397
0.7864	Intermediate Similarity	NPC25401
0.7864	Intermediate Similarity	NPC288110
0.786	Intermediate Similarity	NPC301501
0.7857	Intermediate Similarity	NPC471513
0.7851	Intermediate Similarity	NPC154922
0.7847	Intermediate Similarity	NPC161804
0.7845	Intermediate Similarity	NPC329932
0.7817	Intermediate Similarity	NPC131977
0.7797	Intermediate Similarity	NPC139373
0.7778	Intermediate Similarity	NPC248903
0.7736	Intermediate Similarity	NPC127178
0.7735	Intermediate Similarity	NPC120239
0.7733	Intermediate Similarity	NPC26928
0.7729	Intermediate Similarity	NPC476220
0.7729	Intermediate Similarity	NPC160113
0.7727	Intermediate Similarity	NPC234772
0.7725	Intermediate Similarity	NPC138615
0.7725	Intermediate Similarity	NPC265642
0.7725	Intermediate Similarity	NPC132874
0.7725	Intermediate Similarity	NPC218733
0.7706	Intermediate Similarity	NPC151171
0.7682	Intermediate Similarity	NPC113455
0.7621	Intermediate Similarity	NPC470480
0.7611	Intermediate Similarity	NPC477394
0.7597	Intermediate Similarity	NPC304837
0.7597	Intermediate Similarity	NPC476258
0.7591	Intermediate Similarity	NPC10732
0.7586	Intermediate Similarity	NPC186669
0.7573	Intermediate Similarity	NPC97584
0.7559	Intermediate Similarity	NPC100863
0.7549	Intermediate Similarity	NPC99043
0.7549	Intermediate Similarity	NPC218594
0.7545	Intermediate Similarity	NPC222046
0.7537	Intermediate Similarity	NPC203202
0.7537	Intermediate Similarity	NPC264482
0.7536	Intermediate Similarity	NPC94499
0.7534	Intermediate Similarity	NPC477160
0.7512	Intermediate Similarity	NPC162694
0.7511	Intermediate Similarity	NPC470482
0.7511	Intermediate Similarity	NPC470481
0.7478	Intermediate Similarity	NPC46259
0.7429	Intermediate Similarity	NPC477186
0.7429	Intermediate Similarity	NPC230098
0.7424	Intermediate Similarity	NPC476436
0.7387	Intermediate Similarity	NPC220241
0.7387	Intermediate Similarity	NPC295479
0.7383	Intermediate Similarity	NPC33256
0.738	Intermediate Similarity	NPC122886
0.7379	Intermediate Similarity	NPC6974
0.7356	Intermediate Similarity	NPC474745
0.7345	Intermediate Similarity	NPC182853
0.7327	Intermediate Similarity	NPC67904
0.7327	Intermediate Similarity	NPC138830
0.7325	Intermediate Similarity	NPC118189
0.7308	Intermediate Similarity	NPC474325
0.7304	Intermediate Similarity	NPC115588
0.7294	Intermediate Similarity	NPC469732
0.7285	Intermediate Similarity	NPC478075
0.7273	Intermediate Similarity	NPC268077
0.7265	Intermediate Similarity	NPC476429
0.726	Intermediate Similarity	NPC286135
0.726	Intermediate Similarity	NPC237044
0.726	Intermediate Similarity	NPC474470
0.7256	Intermediate Similarity	NPC243626
0.7251	Intermediate Similarity	NPC474746
0.7251	Intermediate Similarity	NPC475981
0.7249	Intermediate Similarity	NPC76478
0.7244	Intermediate Similarity	NPC321166
0.724	Intermediate Similarity	NPC477161
0.7237	Intermediate Similarity	NPC219397
0.7232	Intermediate Similarity	NPC82541
0.723	Intermediate Similarity	NPC141440
0.7227	Intermediate Similarity	NPC207971
0.7217	Intermediate Similarity	NPC21425
0.7215	Intermediate Similarity	NPC471489
0.7212	Intermediate Similarity	NPC304675
0.72	Intermediate Similarity	NPC116178
0.7195	Intermediate Similarity	NPC470484
0.7193	Intermediate Similarity	NPC87560
0.7193	Intermediate Similarity	NPC134702
0.7191	Intermediate Similarity	NPC474192
0.7191	Intermediate Similarity	NPC475720
0.7182	Intermediate Similarity	NPC474077
0.7177	Intermediate Similarity	NPC35680
0.7176	Intermediate Similarity	NPC230313
0.7168	Intermediate Similarity	NPC217903
0.7163	Intermediate Similarity	NPC196231
0.7161	Intermediate Similarity	NPC473105
0.7156	Intermediate Similarity	NPC17677
0.715	Intermediate Similarity	NPC474708
0.715	Intermediate Similarity	NPC474059
0.7118	Intermediate Similarity	NPC195120
0.7114	Intermediate Similarity	NPC61013
0.7114	Intermediate Similarity	NPC329982
0.7101	Intermediate Similarity	NPC475845
0.71	Intermediate Similarity	NPC7560
0.7093	Intermediate Similarity	NPC114468
0.7085	Intermediate Similarity	NPC80472
0.7083	Intermediate Similarity	NPC204970
0.7083	Intermediate Similarity	NPC475816
0.7067	Intermediate Similarity	NPC168250
0.7062	Intermediate Similarity	NPC15919
0.7059	Intermediate Similarity	NPC249274
0.7059	Intermediate Similarity	NPC471512
0.7059	Intermediate Similarity	NPC205167
0.7054	Intermediate Similarity	NPC11708
0.7054	Intermediate Similarity	NPC198160
0.7053	Intermediate Similarity	NPC57812
0.7053	Intermediate Similarity	NPC474324
0.7051	Intermediate Similarity	NPC470485
0.7051	Intermediate Similarity	NPC285254
0.7044	Intermediate Similarity	NPC248117
0.7042	Intermediate Similarity	NPC473007
0.7033	Intermediate Similarity	NPC470739
0.7033	Intermediate Similarity	NPC477640
0.7033	Intermediate Similarity	NPC225597
0.7032	Intermediate Similarity	NPC272706
0.7028	Intermediate Similarity	NPC99179
0.7019	Intermediate Similarity	NPC475686
0.7019	Intermediate Similarity	NPC82533
0.7019	Intermediate Similarity	NPC290759
0.7019	Intermediate Similarity	NPC58766
0.7019	Intermediate Similarity	NPC158148
0.7019	Intermediate Similarity	NPC266176
0.7018	Intermediate Similarity	NPC268223
0.7005	Intermediate Similarity	NPC473004
0.7005	Intermediate Similarity	NPC63152
0.7	Intermediate Similarity	NPC71124
0.6996	Remote Similarity	NPC250960
0.6996	Remote Similarity	NPC71539
0.6995	Remote Similarity	NPC36495
0.6995	Remote Similarity	NPC193410
0.6991	Remote Similarity	NPC473008
0.6987	Remote Similarity	NPC2905
0.6987	Remote Similarity	NPC298449
0.6987	Remote Similarity	NPC148391
0.6986	Remote Similarity	NPC474475
0.6986	Remote Similarity	NPC311991
0.6983	Remote Similarity	NPC118154
0.6983	Remote Similarity	NPC157983
0.6982	Remote Similarity	NPC254045
0.6982	Remote Similarity	NPC201055
0.6982	Remote Similarity	NPC64576
0.6982	Remote Similarity	NPC151470
0.6979	Remote Similarity	NPC266994
0.6977	Remote Similarity	NPC9867
0.6976	Remote Similarity	NPC158900
0.6971	Remote Similarity	NPC190332
0.6971	Remote Similarity	NPC181653
0.6971	Remote Similarity	NPC100566
0.6959	Remote Similarity	NPC470483
0.6957	Remote Similarity	NPC224970
0.6957	Remote Similarity	NPC223595
0.6957	Remote Similarity	NPC35345
0.6957	Remote Similarity	NPC167724
0.6953	Remote Similarity	NPC329830
0.6952	Remote Similarity	NPC65403
0.6949	Remote Similarity	NPC13249
0.6948	Remote Similarity	NPC32154
0.6947	Remote Similarity	NPC207873
0.6947	Remote Similarity	NPC100573

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 NPC19175 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	575
0.2-0.3	806
0.3-0.4	2191
0.4-0.5	2750
0.5-0.6	2170
0.6-0.7	460
0.7-0.8	7
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
0.7532	Intermediate Similarity	NPD6625	Approved
0.7465	Intermediate Similarity	NPD5582	Discontinued
0.7419	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD2899	Discontinued
0.7234	Intermediate Similarity	NPD6723	Discontinued
0.7098	Intermediate Similarity	NPD4859	Phase 1
0.708	Intermediate Similarity	NPD683	Approved
0.7074	Intermediate Similarity	NPD3940	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4596	Phase 1
0.7051	Intermediate Similarity	NPD7186	Phase 3
0.7048	Intermediate Similarity	NPD4494	Approved
0.7048	Intermediate Similarity	NPD4492	Approved
0.704	Intermediate Similarity	NPD4040	Phase 1
0.7022	Intermediate Similarity	NPD4082	Approved
0.7004	Intermediate Similarity	NPD4493	Discontinued
0.6996	Remote Similarity	NPD6997	Phase 2
0.6991	Remote Similarity	NPD2845	Phase 2
0.6991	Remote Similarity	NPD2843	Phase 2
0.6982	Remote Similarity	NPD2494	Approved
0.6982	Remote Similarity	NPD3450	Approved
0.6982	Remote Similarity	NPD3452	Approved
0.6982	Remote Similarity	NPD2493	Approved
0.6981	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7827	Phase 1
0.6964	Remote Similarity	NPD4582	Approved
0.6964	Remote Similarity	NPD4583	Approved
0.6959	Remote Similarity	NPD2488	Approved
0.6959	Remote Similarity	NPD2490	Approved
0.6955	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4022	Approved
0.6947	Remote Similarity	NPD3472	Approved
0.6943	Remote Similarity	NPD4455	Discontinued
0.6923	Remote Similarity	NPD5071	Phase 2
0.6923	Remote Similarity	NPD4420	Approved
0.692	Remote Similarity	NPD4004	Approved
0.692	Remote Similarity	NPD4002	Approved
0.6916	Remote Similarity	NPD3591	Approved
0.6916	Remote Similarity	NPD3592	Approved
0.6912	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.691	Remote Similarity	NPD3437	Discontinued
0.6903	Remote Similarity	NPD7263	Phase 2
0.69	Remote Similarity	NPD3888	Discontinued
0.6889	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3298	Approved
0.6886	Remote Similarity	NPD3372	Discontinued
0.6886	Remote Similarity	NPD3893	Discontinued
0.6885	Remote Similarity	NPD8465	Approved
0.6885	Remote Similarity	NPD8467	Approved
0.6885	Remote Similarity	NPD8466	Approved
0.6884	Remote Similarity	NPD6851	Approved
0.6884	Remote Similarity	NPD6853	Approved
0.6875	Remote Similarity	NPD5006	Approved
0.6875	Remote Similarity	NPD6107	Approved
0.6875	Remote Similarity	NPD5005	Approved
0.6865	Remote Similarity	NPD7955	Approved
0.6865	Remote Similarity	NPD7956	Approved
0.6863	Remote Similarity	NPD7803	Approved
0.6861	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7048	Phase 3
0.6857	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD1945	Phase 1
0.6848	Remote Similarity	NPD8364	Approved
0.6848	Remote Similarity	NPD8363	Approved
0.684	Remote Similarity	NPD7559	Phase 2
0.6838	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7279	Phase 2
0.6822	Remote Similarity	NPD7278	Phase 2
0.6822	Remote Similarity	NPD3912	Discontinued
0.6814	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2975	Approved
0.6802	Remote Similarity	NPD2973	Approved
0.6802	Remote Similarity	NPD2974	Approved
0.6795	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4580	Approved
0.6783	Remote Similarity	NPD5676	Approved
0.678	Remote Similarity	NPD8460	Approved
0.678	Remote Similarity	NPD8426	Approved
0.678	Remote Similarity	NPD8459	Approved
0.678	Remote Similarity	NPD8425	Approved
0.6776	Remote Similarity	NPD6297	Approved
0.6773	Remote Similarity	NPD3633	Approved
0.6773	Remote Similarity	NPD3634	Approved
0.6771	Remote Similarity	NPD4668	Phase 2
0.6766	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5186	Approved
0.6762	Remote Similarity	NPD5183	Approved
0.6761	Remote Similarity	NPD5313	Approved
0.6761	Remote Similarity	NPD5312	Approved
0.6756	Remote Similarity	NPD6238	Discontinued
0.6756	Remote Similarity	NPD8428	Approved
0.6756	Remote Similarity	NPD8427	Approved
0.6756	Remote Similarity	NPD8429	Approved
0.6756	Remote Similarity	NPD7476	Discontinued
0.6748	Remote Similarity	NPD6517	Phase 3
0.6738	Remote Similarity	NPD7047	Phase 3
0.6738	Remote Similarity	NPD8149	Discontinued
0.6736	Remote Similarity	NPD7922	Phase 1
0.6735	Remote Similarity	NPD7560	Approved
0.6729	Remote Similarity	NPD7479	Phase 2
0.6726	Remote Similarity	NPD3448	Approved
0.6726	Remote Similarity	NPD2491	Approved
0.6726	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3057	Approved
0.6725	Remote Similarity	NPD2906	Approved
0.6725	Remote Similarity	NPD2907	Approved
0.6711	Remote Similarity	NPD4107	Approved
0.6706	Remote Similarity	NPD7708	Approved
0.6698	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2968	Approved
0.6682	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2971	Approved
0.668	Remote Similarity	NPD6199	Discontinued
0.6667	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7891	Discontinued
0.6667	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD5860	Discontinued
0.6667	Remote Similarity	NPD6874	Approved
0.6667	Remote Similarity	NPD3297	Approved
0.6653	Remote Similarity	NPD4846	Phase 2
0.6653	Remote Similarity	NPD5496	Approved
0.6653	Remote Similarity	NPD4111	Phase 1
0.6652	Remote Similarity	NPD2972	Approved
0.6652	Remote Similarity	NPD3533	Approved
0.6652	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7256	Discontinued
0.6636	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6877	Discontinued
0.6621	Remote Similarity	NPD6340	Approved
0.6621	Remote Similarity	NPD6339	Approved
0.662	Remote Similarity	NPD2489	Approved
0.662	Remote Similarity	NPD27	Approved
0.662	Remote Similarity	NPD2898	Approved
0.662	Remote Similarity	NPD4481	Phase 3
0.6608	Remote Similarity	NPD4482	Phase 3
0.6607	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5928	Phase 1
0.6605	Remote Similarity	NPD5600	Discontinued
0.6598	Remote Similarity	NPD6494	Phase 2
0.6594	Remote Similarity	NPD1294	Discontinued
0.6583	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4665	Approved
0.658	Remote Similarity	NPD5658	Approved
0.6577	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2970	Approved
0.6573	Remote Similarity	NPD4083	Discontinued
0.6573	Remote Similarity	NPD2969	Approved
0.6567	Remote Similarity	NPD4206	Approved
0.6565	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8091	Phase 3
0.6561	Remote Similarity	NPD7906	Approved
0.6557	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3983	Phase 3
0.6557	Remote Similarity	NPD4885	Approved
0.6545	Remote Similarity	NPD3006	Discontinued
0.6542	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.654	Remote Similarity	NPD4796	Discontinued
0.6537	Remote Similarity	NPD6296	Discontinued
0.653	Remote Similarity	NPD7280	Phase 3
0.653	Remote Similarity	NPD7310	Approved
0.653	Remote Similarity	NPD7281	Phase 3
0.653	Remote Similarity	NPD7311	Approved
0.653	Remote Similarity	NPD4578	Approved
0.653	Remote Similarity	NPD7313	Approved
0.653	Remote Similarity	NPD7312	Approved
0.653	Remote Similarity	NPD4577	Approved
0.6527	Remote Similarity	NPD7805	Phase 3
0.6526	Remote Similarity	NPD6071	Discontinued
0.6524	Remote Similarity	NPD1742	Approved
0.6524	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD1743	Approved
0.6524	Remote Similarity	NPD19	Approved
0.652	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD3441	Approved
0.6516	Remote Similarity	NPD3442	Approved
0.6516	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7039	Approved
0.6514	Remote Similarity	NPD7038	Approved
0.6513	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8489	Phase 1
0.6502	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7309	Approved
0.6498	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6716	Phase 1
0.6479	Remote Similarity	NPD2681	Approved
0.6479	Remote Similarity	NPD2247	Approved
0.6479	Remote Similarity	NPD2680	Approved
0.6479	Remote Similarity	NPD2249	Approved
0.6478	Remote Similarity	NPD7497	Discontinued
0.6475	Remote Similarity	NPD4981	Phase 2
0.6473	Remote Similarity	NPD7820	Phase 3
0.6471	Remote Similarity	NPD7859	Phase 2

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