NPASS Compound

Structure

CID119329 OpenBabel06191715472D 27 31 0 0 1 0 0 0 0 0999 V2000 -1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -3.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.6180 0.0000 C 0 0 1 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 2.5981 -3.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -4.6180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 14 1 0 0 0 0 4 5 1 0 0 0 0 4 15 2 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 1 1 6 0 0 0 13 18 1 0 0 0 0 13 27 1 0 0 0 0 14 24 2 3 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 16 24 1 1 0 0 0 17 5 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 23 1 6 0 0 0 19 22 1 6 0 0 0 20 23 1 6 0 0 0 21 23 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 3 1 6 0 0 0 23 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	371.25
Volume:	393.04
LogP:	3.567
LogD:	3.335
LogS:	-4.677
# Rotatable Bonds:	2
TPSA:	55.4
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	5.05
Fsp3:	0.826
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.685
MDCK Permeability:	4.0103899664245546e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.242
30% Bioavailability (F30%):	0.097

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.426
Plasma Protein Binding (PPB):	75.23455047607422%
Volume Distribution (VD):	0.945
Pgp-substrate:	9.260618209838867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.215
CYP1A2-substrate:	0.336
CYP2C19-inhibitor:	0.519
CYP2C19-substrate:	0.658
CYP2C9-inhibitor:	0.149
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.149
CYP2D6-substrate:	0.525
CYP3A4-inhibitor:	0.886
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	4.645
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.253
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.775
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.755
Skin Sensitization:	0.946
Carcinogencity:	0.747
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.838

Download Data

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

Natural Product: NPC119329

Natural Product ID:	NPC119329
*Common Name:**	MFYNPKUAXIUSHE-IEGXLHPXSA-N
IUPAC Name:	n.a.
Synonyms:	N-Acetylgitingensine
Standard InCHIKey:	MFYNPKUAXIUSHE-IEGXLHPXSA-N
Standard InCHI:	InChI=1S/C23H33NO3/c1-13-18-6-7-20-17-5-4-15-12-16(24-14(2)25)8-10-22(15,3)19(17)9-11-23(18,20)21(26)27-13/h4,13,16-20H,5-12H2,1-3H3,(H,24,25)/t13-,16+,17+,18+,19-,20-,22-,23-/m0/s1
SMILES:	C[C@H]1[C@H]2CC[C@H]3[C@@H]4CC=C5C[C@@H](CC[C@]5(C)[C@H]4CC[C@]23C(=O)O1)N=C(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801976
PubChem CID:	53355802
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO30860	Kibatalia laurifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443172]
NPO30860	Kibatalia laurifolia	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21443172]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	50000.0	nM	PMID[483547]

☑ 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 NPC119329 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	80
0.1-0.2	634
0.2-0.3	4880
0.3-0.4	17258
0.4-0.5	8874
0.5-0.6	7833
0.6-0.7	2968
0.7-0.8	160
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.88	High Similarity	NPC128698
0.88	High Similarity	NPC239768
0.8738	High Similarity	NPC195841
0.8738	High Similarity	NPC233256
0.8142	Intermediate Similarity	NPC35037
0.8073	Intermediate Similarity	NPC63511
0.8061	Intermediate Similarity	NPC167877
0.8041	Intermediate Similarity	NPC470223
0.802	Intermediate Similarity	NPC470224
0.798	Intermediate Similarity	NPC28227
0.7938	Intermediate Similarity	NPC100391
0.7895	Intermediate Similarity	NPC470276
0.787	Intermediate Similarity	NPC86906
0.785	Intermediate Similarity	NPC98765
0.7714	Intermediate Similarity	NPC475894
0.7652	Intermediate Similarity	NPC470275
0.7647	Intermediate Similarity	NPC471896
0.7619	Intermediate Similarity	NPC322063
0.7611	Intermediate Similarity	NPC469968
0.7611	Intermediate Similarity	NPC80834
0.76	Intermediate Similarity	NPC264127
0.76	Intermediate Similarity	NPC155011
0.7596	Intermediate Similarity	NPC477290
0.7573	Intermediate Similarity	NPC154101
0.7549	Intermediate Similarity	NPC474570
0.7525	Intermediate Similarity	NPC142361
0.7525	Intermediate Similarity	NPC474684
0.7524	Intermediate Similarity	NPC469599
0.7523	Intermediate Similarity	NPC474583
0.7522	Intermediate Similarity	NPC79238
0.7478	Intermediate Similarity	NPC470540
0.7477	Intermediate Similarity	NPC153792
0.7477	Intermediate Similarity	NPC271387
0.7476	Intermediate Similarity	NPC148414
0.7476	Intermediate Similarity	NPC175628
0.7476	Intermediate Similarity	NPC111585
0.7451	Intermediate Similarity	NPC97884
0.7451	Intermediate Similarity	NPC472220
0.7449	Intermediate Similarity	NPC147066
0.7436	Intermediate Similarity	NPC9714
0.7434	Intermediate Similarity	NPC328052
0.7434	Intermediate Similarity	NPC472313
0.7429	Intermediate Similarity	NPC243985
0.7429	Intermediate Similarity	NPC159410
0.7429	Intermediate Similarity	NPC280710
0.7426	Intermediate Similarity	NPC470051
0.7426	Intermediate Similarity	NPC195640
0.7426	Intermediate Similarity	NPC470050
0.7404	Intermediate Similarity	NPC26888
0.7404	Intermediate Similarity	NPC150383
0.74	Intermediate Similarity	NPC165064
0.7391	Intermediate Similarity	NPC106479
0.7387	Intermediate Similarity	NPC36497
0.7383	Intermediate Similarity	NPC240650
0.7379	Intermediate Similarity	NPC474889
0.7379	Intermediate Similarity	NPC474704
0.7379	Intermediate Similarity	NPC475921
0.7368	Intermediate Similarity	NPC474459
0.7364	Intermediate Similarity	NPC140723
0.7364	Intermediate Similarity	NPC36688
0.7353	Intermediate Similarity	NPC96496
0.7353	Intermediate Similarity	NPC187376
0.7353	Intermediate Similarity	NPC159046
0.7353	Intermediate Similarity	NPC233836
0.7347	Intermediate Similarity	NPC170038
0.7333	Intermediate Similarity	NPC470375
0.7333	Intermediate Similarity	NPC474436
0.7333	Intermediate Similarity	NPC107674
0.7333	Intermediate Similarity	NPC470376
0.7333	Intermediate Similarity	NPC49776
0.7333	Intermediate Similarity	NPC141497
0.7333	Intermediate Similarity	NPC63118
0.7333	Intermediate Similarity	NPC170220
0.7327	Intermediate Similarity	NPC75810
0.7327	Intermediate Similarity	NPC323765
0.7327	Intermediate Similarity	NPC474218
0.7308	Intermediate Similarity	NPC44240
0.7304	Intermediate Similarity	NPC474452
0.7297	Intermediate Similarity	NPC472227
0.7297	Intermediate Similarity	NPC475239
0.7297	Intermediate Similarity	NPC255309
0.7297	Intermediate Similarity	NPC471293
0.7297	Intermediate Similarity	NPC472228
0.7282	Intermediate Similarity	NPC474845
0.7282	Intermediate Similarity	NPC294480
0.7273	Intermediate Similarity	NPC471083
0.7273	Intermediate Similarity	NPC38350
0.7273	Intermediate Similarity	NPC232625
0.7273	Intermediate Similarity	NPC201912
0.7264	Intermediate Similarity	NPC471720
0.7264	Intermediate Similarity	NPC56525
0.7255	Intermediate Similarity	NPC55309
0.7255	Intermediate Similarity	NPC28252
0.7255	Intermediate Similarity	NPC325594
0.7248	Intermediate Similarity	NPC476303
0.7245	Intermediate Similarity	NPC477371
0.7245	Intermediate Similarity	NPC118987
0.7245	Intermediate Similarity	NPC44083
0.7245	Intermediate Similarity	NPC153987
0.7238	Intermediate Similarity	NPC189520
0.7238	Intermediate Similarity	NPC297265
0.7238	Intermediate Similarity	NPC476064
0.7238	Intermediate Similarity	NPC86266
0.7238	Intermediate Similarity	NPC212301
0.7238	Intermediate Similarity	NPC218301
0.7238	Intermediate Similarity	NPC110657
0.7232	Intermediate Similarity	NPC96377
0.7228	Intermediate Similarity	NPC85774
0.7228	Intermediate Similarity	NPC82902
0.7228	Intermediate Similarity	NPC59453
0.7228	Intermediate Similarity	NPC221758
0.7228	Intermediate Similarity	NPC214043
0.7222	Intermediate Similarity	NPC57416
0.7222	Intermediate Similarity	NPC4834
0.7222	Intermediate Similarity	NPC107243
0.7212	Intermediate Similarity	NPC215029
0.7212	Intermediate Similarity	NPC102414
0.7212	Intermediate Similarity	NPC54689
0.7212	Intermediate Similarity	NPC476733
0.7212	Intermediate Similarity	NPC249312
0.7212	Intermediate Similarity	NPC77168
0.7212	Intermediate Similarity	NPC84271
0.72	Intermediate Similarity	NPC320514
0.72	Intermediate Similarity	NPC240302
0.72	Intermediate Similarity	NPC133391
0.72	Intermediate Similarity	NPC260956
0.7196	Intermediate Similarity	NPC69548
0.7196	Intermediate Similarity	NPC279974
0.7196	Intermediate Similarity	NPC184848
0.7184	Intermediate Similarity	NPC312215
0.7182	Intermediate Similarity	NPC474327
0.717	Intermediate Similarity	NPC152897
0.717	Intermediate Similarity	NPC66429
0.7168	Intermediate Similarity	NPC169375
0.7168	Intermediate Similarity	NPC59530
0.7168	Intermediate Similarity	NPC220974
0.7168	Intermediate Similarity	NPC25340
0.7157	Intermediate Similarity	NPC329738
0.7157	Intermediate Similarity	NPC471224
0.7157	Intermediate Similarity	NPC283733
0.7157	Intermediate Similarity	NPC29447
0.7156	Intermediate Similarity	NPC140685
0.7156	Intermediate Similarity	NPC477813
0.7143	Intermediate Similarity	NPC477288
0.7143	Intermediate Similarity	NPC474964
0.7143	Intermediate Similarity	NPC139585
0.7143	Intermediate Similarity	NPC35574
0.713	Intermediate Similarity	NPC327788
0.713	Intermediate Similarity	NPC307164
0.713	Intermediate Similarity	NPC72753
0.7129	Intermediate Similarity	NPC470047
0.7129	Intermediate Similarity	NPC21667
0.7129	Intermediate Similarity	NPC69279
0.7129	Intermediate Similarity	NPC83569
0.7129	Intermediate Similarity	NPC470046
0.7129	Intermediate Similarity	NPC470948
0.7129	Intermediate Similarity	NPC471037
0.7129	Intermediate Similarity	NPC167103
0.7117	Intermediate Similarity	NPC50815
0.7117	Intermediate Similarity	NPC152718
0.7117	Intermediate Similarity	NPC476755
0.7115	Intermediate Similarity	NPC229407
0.7115	Intermediate Similarity	NPC250687
0.7115	Intermediate Similarity	NPC242864
0.7115	Intermediate Similarity	NPC254572
0.7115	Intermediate Similarity	NPC183546
0.7115	Intermediate Similarity	NPC48824
0.7103	Intermediate Similarity	NPC49670
0.7103	Intermediate Similarity	NPC472223
0.7103	Intermediate Similarity	NPC472224
0.71	Intermediate Similarity	NPC474955
0.71	Intermediate Similarity	NPC327002
0.71	Intermediate Similarity	NPC477372
0.7091	Intermediate Similarity	NPC218383
0.7091	Intermediate Similarity	NPC167974
0.7091	Intermediate Similarity	NPC201406
0.7087	Intermediate Similarity	NPC51014
0.7087	Intermediate Similarity	NPC31564
0.7087	Intermediate Similarity	NPC474970
0.7087	Intermediate Similarity	NPC145879
0.7087	Intermediate Similarity	NPC474778
0.7087	Intermediate Similarity	NPC6979
0.7087	Intermediate Similarity	NPC469994
0.7087	Intermediate Similarity	NPC212843
0.7087	Intermediate Similarity	NPC474732
0.7087	Intermediate Similarity	NPC474733
0.7087	Intermediate Similarity	NPC73038
0.708	Intermediate Similarity	NPC230677
0.7075	Intermediate Similarity	NPC262870
0.7075	Intermediate Similarity	NPC23434
0.7071	Intermediate Similarity	NPC327674
0.7071	Intermediate Similarity	NPC158846
0.7064	Intermediate Similarity	NPC292133
0.7059	Intermediate Similarity	NPC194937
0.7059	Intermediate Similarity	NPC109512
0.7059	Intermediate Similarity	NPC473246
0.7059	Intermediate Similarity	NPC476038
0.7054	Intermediate Similarity	NPC293299
0.7054	Intermediate Similarity	NPC45365
0.7054	Intermediate Similarity	NPC176883

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 NPC119329 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	83
0.1-0.2	448
0.2-0.3	2837
0.3-0.4	4119
0.4-0.5	1084
0.5-0.6	375
0.6-0.7	182
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
0.7788	Intermediate Similarity	NPD5349	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6399	Phase 3
0.7451	Intermediate Similarity	NPD6903	Approved
0.7426	Intermediate Similarity	NPD5330	Approved
0.7426	Intermediate Similarity	NPD6409	Approved
0.7426	Intermediate Similarity	NPD6684	Approved
0.7426	Intermediate Similarity	NPD7334	Approved
0.7426	Intermediate Similarity	NPD7146	Approved
0.7426	Intermediate Similarity	NPD7521	Approved
0.7407	Intermediate Similarity	NPD6404	Discontinued
0.7282	Intermediate Similarity	NPD6672	Approved
0.7282	Intermediate Similarity	NPD5737	Approved
0.7282	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5769	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4786	Approved
0.7196	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6420	Discontinued
0.7091	Intermediate Similarity	NPD8418	Phase 2
0.7087	Intermediate Similarity	NPD6098	Approved
0.7064	Intermediate Similarity	NPD6083	Phase 2
0.7064	Intermediate Similarity	NPD6084	Phase 2
0.703	Intermediate Similarity	NPD3667	Approved
0.7009	Intermediate Similarity	NPD5781	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5696	Approved
0.6981	Remote Similarity	NPD5207	Approved
0.6944	Remote Similarity	NPD5707	Approved
0.6944	Remote Similarity	NPD6001	Approved
0.6923	Remote Similarity	NPD3618	Phase 1
0.6916	Remote Similarity	NPD8034	Phase 2
0.6916	Remote Similarity	NPD8035	Phase 2
0.6893	Remote Similarity	NPD3665	Phase 1
0.6893	Remote Similarity	NPD3133	Approved
0.6893	Remote Similarity	NPD3666	Approved
0.6887	Remote Similarity	NPD5328	Approved
0.6887	Remote Similarity	NPD6904	Approved
0.6887	Remote Similarity	NPD6080	Approved
0.6887	Remote Similarity	NPD6673	Approved
0.6881	Remote Similarity	NPD5695	Phase 3
0.6829	Remote Similarity	NPD6909	Approved
0.6829	Remote Similarity	NPD6908	Approved
0.6827	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7320	Approved
0.6792	Remote Similarity	NPD5208	Approved
0.6789	Remote Similarity	NPD7748	Approved
0.6789	Remote Similarity	NPD5771	Approved
0.6783	Remote Similarity	NPD7128	Approved
0.6783	Remote Similarity	NPD5739	Approved
0.6783	Remote Similarity	NPD6675	Approved
0.6783	Remote Similarity	NPD6008	Approved
0.6783	Remote Similarity	NPD6402	Approved
0.6759	Remote Similarity	NPD6079	Approved
0.6757	Remote Similarity	NPD7902	Approved
0.6752	Remote Similarity	NPD6372	Approved
0.6752	Remote Similarity	NPD6373	Approved
0.6731	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD4223	Phase 3
0.6699	Remote Similarity	NPD4221	Approved
0.6692	Remote Similarity	NPD6334	Approved
0.6692	Remote Similarity	NPD6333	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD7517	Approved
0.6667	Remote Similarity	NPD7519	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD7518	Approved
0.6639	Remote Similarity	NPD6650	Approved
0.6639	Remote Similarity	NPD6649	Approved
0.6636	Remote Similarity	NPD7900	Approved
0.6636	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6052	Approved
0.6606	Remote Similarity	NPD6050	Approved
0.6606	Remote Similarity	NPD5693	Phase 1
0.6606	Remote Similarity	NPD5281	Approved
0.6606	Remote Similarity	NPD7515	Phase 2
0.6606	Remote Similarity	NPD5284	Approved
0.6604	Remote Similarity	NPD5279	Phase 3
0.6587	Remote Similarity	NPD7122	Discontinued
0.6581	Remote Similarity	NPD5697	Approved
0.6581	Remote Similarity	NPD5701	Approved
0.6574	Remote Similarity	NPD4753	Phase 2
0.6574	Remote Similarity	NPD6051	Approved
0.6571	Remote Similarity	NPD4197	Approved
0.6555	Remote Similarity	NPD6883	Approved
0.6555	Remote Similarity	NPD7102	Approved
0.6555	Remote Similarity	NPD7290	Approved
0.6549	Remote Similarity	NPD7638	Approved
0.6545	Remote Similarity	NPD4202	Approved
0.6525	Remote Similarity	NPD6011	Approved
0.6518	Remote Similarity	NPD4697	Phase 3
0.6514	Remote Similarity	NPD5692	Phase 3
0.65	Remote Similarity	NPD6847	Approved
0.65	Remote Similarity	NPD6869	Approved
0.65	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6942	Approved
0.65	Remote Similarity	NPD8130	Phase 1
0.65	Remote Similarity	NPD6617	Approved
0.65	Remote Similarity	NPD7339	Approved
0.6496	Remote Similarity	NPD7333	Discontinued
0.6491	Remote Similarity	NPD7640	Approved
0.6491	Remote Similarity	NPD7639	Approved
0.6471	Remote Similarity	NPD6012	Approved
0.6471	Remote Similarity	NPD6013	Approved
0.6471	Remote Similarity	NPD6014	Approved
0.6455	Remote Similarity	NPD5694	Approved
0.6449	Remote Similarity	NPD5205	Approved
0.6449	Remote Similarity	NPD4138	Approved
0.6449	Remote Similarity	NPD4690	Approved
0.6449	Remote Similarity	NPD4688	Approved
0.6449	Remote Similarity	NPD4689	Approved
0.6449	Remote Similarity	NPD4693	Phase 3
0.6446	Remote Similarity	NPD6882	Approved
0.6446	Remote Similarity	NPD8297	Approved
0.6429	Remote Similarity	NPD5210	Approved
0.6429	Remote Similarity	NPD4629	Approved
0.6412	Remote Similarity	NPD6914	Discontinued
0.6393	Remote Similarity	NPD8298	Phase 2
0.6381	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5222	Approved
0.6372	Remote Similarity	NPD5221	Approved
0.6372	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD4096	Approved
0.6355	Remote Similarity	NPD1694	Approved
0.6349	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7147	Phase 3
0.633	Remote Similarity	NPD4723	Approved
0.633	Remote Similarity	NPD4722	Approved
0.6328	Remote Similarity	NPD7604	Phase 2
0.6321	Remote Similarity	NPD4788	Approved
0.6316	Remote Similarity	NPD4755	Approved
0.6316	Remote Similarity	NPD5173	Approved
0.6311	Remote Similarity	NPD3617	Approved
0.6306	Remote Similarity	NPD6411	Approved
0.6303	Remote Similarity	NPD6412	Phase 2
0.6299	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5690	Phase 2
0.6296	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5280	Approved
0.6296	Remote Similarity	NPD4694	Approved
0.629	Remote Similarity	NPD6868	Approved
0.6286	Remote Similarity	NPD857	Phase 3
0.6275	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4747	Approved
0.626	Remote Similarity	NPD8336	Approved
0.626	Remote Similarity	NPD8337	Approved
0.6239	Remote Similarity	NPD3573	Approved
0.6238	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7732	Phase 3
0.6228	Remote Similarity	NPD7614	Phase 1
0.6207	Remote Similarity	NPD5286	Approved
0.6207	Remote Similarity	NPD4700	Approved
0.6207	Remote Similarity	NPD4696	Approved
0.6207	Remote Similarity	NPD5285	Approved
0.62	Remote Similarity	NPD5777	Approved
0.62	Remote Similarity	NPD4243	Approved
0.6194	Remote Similarity	NPD6845	Suspended
0.619	Remote Similarity	NPD6335	Approved
0.619	Remote Similarity	NPD7525	Registered
0.6176	Remote Similarity	NPD3702	Approved
0.6172	Remote Similarity	NPD5981	Approved
0.6168	Remote Similarity	NPD5362	Discontinued
0.6167	Remote Similarity	NPD6614	Approved
0.6162	Remote Similarity	NPD4137	Phase 3
0.6161	Remote Similarity	NPD7637	Suspended
0.616	Remote Similarity	NPD7755	Approved
0.616	Remote Similarity	NPD7754	Approved
0.616	Remote Similarity	NPD6274	Approved
0.6154	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7492	Approved
0.6154	Remote Similarity	NPD5223	Approved
0.6148	Remote Similarity	NPD6421	Discontinued
0.6142	Remote Similarity	NPD7101	Approved
0.6142	Remote Similarity	NPD7100	Approved
0.614	Remote Similarity	NPD5654	Approved
0.6132	Remote Similarity	NPD4139	Approved
0.6132	Remote Similarity	NPD4692	Approved
0.6129	Remote Similarity	NPD4632	Approved
0.6126	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6101	Approved
0.6119	Remote Similarity	NPD7260	Phase 2
0.6117	Remote Similarity	NPD6117	Approved
0.6111	Remote Similarity	NPD6317	Approved
0.6107	Remote Similarity	NPD6616	Approved
0.6102	Remote Similarity	NPD5224	Approved
0.6102	Remote Similarity	NPD5211	Phase 2
0.6102	Remote Similarity	NPD5226	Approved
0.6102	Remote Similarity	NPD5225	Approved
0.6102	Remote Similarity	NPD4633	Approved
0.61	Remote Similarity	NPD4691	Approved
0.6098	Remote Similarity	NPD3643	Approved
0.6098	Remote Similarity	NPD3642	Approved
0.6098	Remote Similarity	NPD3644	Approved
0.6095	Remote Similarity	NPD4195	Approved
0.6094	Remote Similarity	NPD6059	Approved
0.6094	Remote Similarity	NPD6054	Approved
0.6083	Remote Similarity	NPD6920	Discontinued
0.6078	Remote Similarity	NPD4784	Approved
0.6078	Remote Similarity	NPD4785	Approved
0.6078	Remote Similarity	NPD6926	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