NPASS Compound

Structure

NPC33398 OpenBabel07101718302D 26 30 0 0 1 0 0 0 0 0999 V2000 4.0050 -0.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9305 -0.7971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6085 -0.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7425 -0.6399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1444 0.8601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0104 1.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8025 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7425 1.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3095 1.6101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0415 2.1101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6085 0.8601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8765 -0.1399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1444 -0.1399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0104 -0.6399 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8765 0.8601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1755 1.6101 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9075 1.6101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1755 2.6101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 -1.3849 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 25 1 0 0 0 0 3 4 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 9 13 1 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 11 21 1 0 0 0 0 12 21 1 0 0 0 0 12 22 1 0 0 0 0 13 21 1 6 0 0 0 14 18 1 1 0 0 0 14 19 1 0 0 0 0 15 18 1 1 0 0 0 15 20 1 0 0 0 0 16 25 1 1 0 0 0 16 26 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 1 1 1 0 0 0 19 6 1 1 0 0 0 20 8 1 6 0 0 0 21 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.22
Volume:	370.305
LogP:	2.034
LogD:	2.192
LogS:	-3.931
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	6.416
Fsp3:	0.952
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.2
MDCK Permeability:	1.7326063243672252e-05
Pgp-inhibitor:	0.779
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.079

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	83.76419830322266%
Volume Distribution (VD):	0.692
Pgp-substrate:	11.668678283691406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.808
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.736
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.886
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	5.258
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.624
Drug-inuced Liver Injury (DILI):	0.085
AMES Toxicity:	0.706
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.769
Carcinogencity:	0.651
Eye Corrosion:	0.021
Eye Irritation:	0.041
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC33398

Natural Product ID:	NPC33398
*Common Name:**	JGJQQOVNDDCZBN-ADGKCSTMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JGJQQOVNDDCZBN-ADGKCSTMSA-N
Standard InCHI:	InChI=1S/C21H32O5/c1-18-7-8-20(10-16(25-2)26-17(20)23)15(18)5-6-19-9-13(3-4-14(18)19)21(24,11-19)12-22/h13-16,22,24H,3-12H2,1-2H3/t13-,14+,15+,16+,18+,19+,20-,21+/m1/s1
SMILES:	C[C@]12CC[C@@]3(C[C@@H](OC)OC3=O)[C@H]2CC[C@]23C[C@@H](CC[C@@H]13)[C@](C2)(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586297
PubChem CID:	n.a.
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
NPO32576	tricalysia fruticosa	Species	Rubiaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[26052978]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[465108]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	>	90.0	%	PMID[465108]

☑ 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 NPC33398 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	386
0.1-0.2	3578
0.2-0.3	13931
0.3-0.4	10004
0.4-0.5	6018
0.5-0.6	6573
0.6-0.7	1934
0.7-0.8	260
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC472237
0.8667	High Similarity	NPC472238
0.8462	Intermediate Similarity	NPC472232
0.8462	Intermediate Similarity	NPC472231
0.8333	Intermediate Similarity	NPC476732
0.8333	Intermediate Similarity	NPC199965
0.828	Intermediate Similarity	NPC215570
0.8256	Intermediate Similarity	NPC472229
0.8256	Intermediate Similarity	NPC472230
0.8214	Intermediate Similarity	NPC180199
0.8214	Intermediate Similarity	NPC477919
0.8161	Intermediate Similarity	NPC477935
0.8161	Intermediate Similarity	NPC311642
0.8161	Intermediate Similarity	NPC164289
0.8161	Intermediate Similarity	NPC242771
0.8161	Intermediate Similarity	NPC100366
0.814	Intermediate Similarity	NPC472853
0.8	Intermediate Similarity	NPC92139
0.798	Intermediate Similarity	NPC100078
0.7979	Intermediate Similarity	NPC206878
0.7979	Intermediate Similarity	NPC470424
0.7978	Intermediate Similarity	NPC79308
0.7959	Intermediate Similarity	NPC213528
0.7959	Intermediate Similarity	NPC244969
0.7955	Intermediate Similarity	NPC148740
0.7955	Intermediate Similarity	NPC477936
0.7955	Intermediate Similarity	NPC102156
0.7935	Intermediate Similarity	NPC472234
0.7935	Intermediate Similarity	NPC472233
0.79	Intermediate Similarity	NPC166079
0.7865	Intermediate Similarity	NPC259173
0.7857	Intermediate Similarity	NPC478181
0.7841	Intermediate Similarity	NPC58631
0.7826	Intermediate Similarity	NPC470009
0.7812	Intermediate Similarity	NPC116683
0.7723	Intermediate Similarity	NPC306776
0.7708	Intermediate Similarity	NPC21897
0.7684	Intermediate Similarity	NPC256104
0.7684	Intermediate Similarity	NPC211845
0.7684	Intermediate Similarity	NPC122083
0.7684	Intermediate Similarity	NPC182740
0.7684	Intermediate Similarity	NPC161035
0.7647	Intermediate Similarity	NPC472944
0.7647	Intermediate Similarity	NPC472854
0.7647	Intermediate Similarity	NPC472945
0.7642	Intermediate Similarity	NPC79193
0.7629	Intermediate Similarity	NPC475785
0.7629	Intermediate Similarity	NPC476728
0.7624	Intermediate Similarity	NPC472227
0.7624	Intermediate Similarity	NPC472228
0.7619	Intermediate Similarity	NPC469940
0.7609	Intermediate Similarity	NPC474448
0.7609	Intermediate Similarity	NPC472272
0.7604	Intermediate Similarity	NPC470423
0.7596	Intermediate Similarity	NPC106760
0.7586	Intermediate Similarity	NPC474404
0.7586	Intermediate Similarity	NPC171658
0.7582	Intermediate Similarity	NPC101138
0.7582	Intermediate Similarity	NPC25802
0.7582	Intermediate Similarity	NPC51135
0.7582	Intermediate Similarity	NPC82492
0.7579	Intermediate Similarity	NPC474065
0.7579	Intermediate Similarity	NPC475878
0.7576	Intermediate Similarity	NPC20028
0.7558	Intermediate Similarity	NPC27349
0.7558	Intermediate Similarity	NPC24014
0.7551	Intermediate Similarity	NPC74466
0.7551	Intermediate Similarity	NPC472273
0.7551	Intermediate Similarity	NPC470632
0.7549	Intermediate Similarity	NPC215408
0.7527	Intermediate Similarity	NPC239938
0.75	Intermediate Similarity	NPC477929
0.75	Intermediate Similarity	NPC477172
0.75	Intermediate Similarity	NPC178853
0.7475	Intermediate Similarity	NPC292775
0.7473	Intermediate Similarity	NPC268578
0.7473	Intermediate Similarity	NPC217559
0.7473	Intermediate Similarity	NPC292458
0.7471	Intermediate Similarity	NPC477932
0.7471	Intermediate Similarity	NPC477933
0.7451	Intermediate Similarity	NPC88469
0.7449	Intermediate Similarity	NPC193785
0.7449	Intermediate Similarity	NPC475765
0.7447	Intermediate Similarity	NPC229407
0.7447	Intermediate Similarity	NPC48824
0.7447	Intermediate Similarity	NPC254572
0.7447	Intermediate Similarity	NPC255176
0.7447	Intermediate Similarity	NPC250687
0.7447	Intermediate Similarity	NPC221993
0.7444	Intermediate Similarity	NPC232625
0.7444	Intermediate Similarity	NPC12933
0.7426	Intermediate Similarity	NPC310031
0.7426	Intermediate Similarity	NPC80191
0.7419	Intermediate Similarity	NPC470657
0.7416	Intermediate Similarity	NPC245029
0.7416	Intermediate Similarity	NPC31302
0.7412	Intermediate Similarity	NPC197701
0.7404	Intermediate Similarity	NPC475319
0.7404	Intermediate Similarity	NPC92890
0.7404	Intermediate Similarity	NPC224414
0.7404	Intermediate Similarity	NPC202898
0.74	Intermediate Similarity	NPC470030
0.74	Intermediate Similarity	NPC41843
0.7396	Intermediate Similarity	NPC150383
0.7396	Intermediate Similarity	NPC471747
0.7391	Intermediate Similarity	NPC18953
0.7391	Intermediate Similarity	NPC291310
0.7386	Intermediate Similarity	NPC207010
0.7386	Intermediate Similarity	NPC317913
0.7386	Intermediate Similarity	NPC70996
0.7386	Intermediate Similarity	NPC477918
0.7386	Intermediate Similarity	NPC307865
0.7383	Intermediate Similarity	NPC102619
0.7381	Intermediate Similarity	NPC252032
0.7381	Intermediate Similarity	NPC469941
0.7381	Intermediate Similarity	NPC319671
0.7381	Intermediate Similarity	NPC476734
0.7374	Intermediate Similarity	NPC471241
0.7368	Intermediate Similarity	NPC269267
0.7368	Intermediate Similarity	NPC215029
0.7368	Intermediate Similarity	NPC476733
0.7363	Intermediate Similarity	NPC121121
0.7363	Intermediate Similarity	NPC24556
0.7363	Intermediate Similarity	NPC317066
0.7358	Intermediate Similarity	NPC469824
0.7358	Intermediate Similarity	NPC473062
0.7356	Intermediate Similarity	NPC477934
0.7347	Intermediate Similarity	NPC305808
0.734	Intermediate Similarity	NPC472396
0.734	Intermediate Similarity	NPC5943
0.734	Intermediate Similarity	NPC31349
0.734	Intermediate Similarity	NPC210658
0.734	Intermediate Similarity	NPC161928
0.734	Intermediate Similarity	NPC252714
0.7339	Intermediate Similarity	NPC179429
0.7333	Intermediate Similarity	NPC208333
0.7333	Intermediate Similarity	NPC473817
0.7333	Intermediate Similarity	NPC220836
0.7333	Intermediate Similarity	NPC273002
0.7333	Intermediate Similarity	NPC170038
0.7333	Intermediate Similarity	NPC227879
0.7333	Intermediate Similarity	NPC470609
0.7333	Intermediate Similarity	NPC92297
0.7333	Intermediate Similarity	NPC233433
0.7333	Intermediate Similarity	NPC94086
0.7327	Intermediate Similarity	NPC476512
0.7327	Intermediate Similarity	NPC108227
0.7327	Intermediate Similarity	NPC475574
0.7327	Intermediate Similarity	NPC472081
0.732	Intermediate Similarity	NPC475307
0.7308	Intermediate Similarity	NPC203974
0.7303	Intermediate Similarity	NPC471045
0.729	Intermediate Similarity	NPC477489
0.7283	Intermediate Similarity	NPC2572
0.7283	Intermediate Similarity	NPC477285
0.7283	Intermediate Similarity	NPC472847
0.7283	Intermediate Similarity	NPC29342
0.7283	Intermediate Similarity	NPC111582
0.7283	Intermediate Similarity	NPC472744
0.7282	Intermediate Similarity	NPC100955
0.7282	Intermediate Similarity	NPC470167
0.7282	Intermediate Similarity	NPC121566
0.7273	Intermediate Similarity	NPC156377
0.7273	Intermediate Similarity	NPC237071
0.7273	Intermediate Similarity	NPC203434
0.7273	Intermediate Similarity	NPC238796
0.7273	Intermediate Similarity	NPC4209
0.7264	Intermediate Similarity	NPC101450
0.7263	Intermediate Similarity	NPC471221
0.7263	Intermediate Similarity	NPC128475
0.7255	Intermediate Similarity	NPC94919
0.7255	Intermediate Similarity	NPC470172
0.7255	Intermediate Similarity	NPC292803
0.7255	Intermediate Similarity	NPC310138
0.7255	Intermediate Similarity	NPC114700
0.7255	Intermediate Similarity	NPC470029
0.7255	Intermediate Similarity	NPC134967
0.7253	Intermediate Similarity	NPC77311
0.7253	Intermediate Similarity	NPC271572
0.7253	Intermediate Similarity	NPC474870
0.7245	Intermediate Similarity	NPC472223
0.7245	Intermediate Similarity	NPC472224
0.7241	Intermediate Similarity	NPC477930
0.7241	Intermediate Similarity	NPC167702
0.7241	Intermediate Similarity	NPC280026
0.7238	Intermediate Similarity	NPC472079
0.7234	Intermediate Similarity	NPC471411
0.7234	Intermediate Similarity	NPC471410
0.7234	Intermediate Similarity	NPC131365
0.7234	Intermediate Similarity	NPC80700
0.7234	Intermediate Similarity	NPC80590
0.7222	Intermediate Similarity	NPC97002
0.7222	Intermediate Similarity	NPC472310
0.7222	Intermediate Similarity	NPC118987
0.7222	Intermediate Similarity	NPC474754
0.7222	Intermediate Similarity	NPC201276
0.7222	Intermediate Similarity	NPC80891
0.7212	Intermediate Similarity	NPC63023
0.7212	Intermediate Similarity	NPC95243
0.7204	Intermediate Similarity	NPC227260

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 NPC33398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	3713
0.2-0.3	3500
0.3-0.4	869
0.4-0.5	292
0.5-0.6	240
0.6-0.7	104
0.7-0.8	2
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
0.7765	Intermediate Similarity	NPD3702	Approved
0.7451	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6116	Phase 1
0.7273	Intermediate Similarity	NPD6117	Approved
0.7241	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5777	Approved
0.7115	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6114	Approved
0.7111	Intermediate Similarity	NPD6115	Approved
0.7111	Intermediate Similarity	NPD6118	Approved
0.7111	Intermediate Similarity	NPD6697	Approved
0.7108	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4245	Approved
0.7093	Intermediate Similarity	NPD4244	Approved
0.7011	Intermediate Similarity	NPD6081	Approved
0.6977	Remote Similarity	NPD3698	Phase 2
0.697	Remote Similarity	NPD8171	Discontinued
0.6957	Remote Similarity	NPD6928	Phase 2
0.6897	Remote Similarity	NPD4789	Approved
0.6824	Remote Similarity	NPD4224	Phase 2
0.6822	Remote Similarity	NPD6412	Phase 2
0.6818	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8133	Approved
0.67	Remote Similarity	NPD8034	Phase 2
0.67	Remote Similarity	NPD8035	Phase 2
0.6699	Remote Similarity	NPD6084	Phase 2
0.6699	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6399	Phase 3
0.6606	Remote Similarity	NPD7320	Approved
0.6591	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4788	Approved
0.6562	Remote Similarity	NPD3669	Approved
0.6559	Remote Similarity	NPD4238	Approved
0.6559	Remote Similarity	NPD4802	Phase 2
0.6555	Remote Similarity	NPD7507	Approved
0.6526	Remote Similarity	NPD1780	Approved
0.6526	Remote Similarity	NPD1779	Approved
0.6518	Remote Similarity	NPD6882	Approved
0.6506	Remote Similarity	NPD3198	Approved
0.6505	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD7078	Approved
0.6491	Remote Similarity	NPD6940	Discontinued
0.6476	Remote Similarity	NPD5696	Approved
0.6446	Remote Similarity	NPD7736	Approved
0.6441	Remote Similarity	NPD6370	Approved
0.6429	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6675	Approved
0.6422	Remote Similarity	NPD6402	Approved
0.6422	Remote Similarity	NPD5739	Approved
0.6422	Remote Similarity	NPD7128	Approved
0.6404	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6903	Approved
0.6396	Remote Similarity	NPD6373	Approved
0.6396	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6372	Approved
0.6393	Remote Similarity	NPD7319	Approved
0.6346	Remote Similarity	NPD5695	Phase 3
0.6333	Remote Similarity	NPD7492	Approved
0.6306	Remote Similarity	NPD6686	Approved
0.6306	Remote Similarity	NPD6899	Approved
0.6306	Remote Similarity	NPD6881	Approved
0.6283	Remote Similarity	NPD6649	Approved
0.6283	Remote Similarity	NPD6650	Approved
0.6281	Remote Similarity	NPD6616	Approved
0.6271	Remote Similarity	NPD6059	Approved
0.6271	Remote Similarity	NPD6054	Approved
0.6264	Remote Similarity	NPD4758	Discontinued
0.6239	Remote Similarity	NPD7327	Approved
0.6239	Remote Similarity	NPD7328	Approved
0.6237	Remote Similarity	NPD3703	Phase 2
0.6228	Remote Similarity	NPD8297	Approved
0.6216	Remote Similarity	NPD5701	Approved
0.6216	Remote Similarity	NPD5697	Approved
0.6214	Remote Similarity	NPD5281	Approved
0.6214	Remote Similarity	NPD5284	Approved
0.6211	Remote Similarity	NPD5364	Discontinued
0.62	Remote Similarity	NPD7146	Approved
0.62	Remote Similarity	NPD6409	Approved
0.62	Remote Similarity	NPD7334	Approved
0.62	Remote Similarity	NPD7521	Approved
0.62	Remote Similarity	NPD5330	Approved
0.62	Remote Similarity	NPD6684	Approved
0.62	Remote Similarity	NPD6098	Approved
0.6195	Remote Similarity	NPD7290	Approved
0.6195	Remote Similarity	NPD6883	Approved
0.6195	Remote Similarity	NPD7102	Approved
0.6186	Remote Similarity	NPD7516	Approved
0.6176	Remote Similarity	NPD4753	Phase 2
0.6176	Remote Similarity	NPD6080	Approved
0.6176	Remote Similarity	NPD6904	Approved
0.6176	Remote Similarity	NPD6673	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD6009	Approved
0.6154	Remote Similarity	NPD4787	Phase 1
0.614	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD6869	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6617	Approved
0.614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8377	Approved
0.6134	Remote Similarity	NPD8294	Approved
0.6126	Remote Similarity	NPD6008	Approved
0.6117	Remote Similarity	NPD5207	Approved
0.6116	Remote Similarity	NPD6067	Discontinued
0.6116	Remote Similarity	NPD7122	Discontinued
0.6106	Remote Similarity	NPD6012	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6106	Remote Similarity	NPD6014	Approved
0.6095	Remote Similarity	NPD6001	Approved
0.6083	Remote Similarity	NPD8379	Approved
0.6083	Remote Similarity	NPD8335	Approved
0.6083	Remote Similarity	NPD6015	Approved
0.6083	Remote Similarity	NPD6016	Approved
0.6083	Remote Similarity	NPD8296	Approved
0.6083	Remote Similarity	NPD8378	Approved
0.6083	Remote Similarity	NPD8033	Approved
0.6083	Remote Similarity	NPD8380	Approved
0.6078	Remote Similarity	NPD6672	Approved
0.6078	Remote Similarity	NPD5737	Approved
0.6078	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD2257	Approved
0.6042	Remote Similarity	NPD3671	Phase 1
0.6038	Remote Similarity	NPD4629	Approved
0.6038	Remote Similarity	NPD5210	Approved
0.6038	Remote Similarity	NPD7991	Discontinued
0.6034	Remote Similarity	NPD4632	Approved
0.6033	Remote Similarity	NPD5988	Approved
0.6017	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD4786	Approved
0.596	Remote Similarity	NPD4221	Approved
0.596	Remote Similarity	NPD4223	Phase 3
0.5957	Remote Similarity	NPD1810	Approved
0.5957	Remote Similarity	NPD1811	Approved
0.595	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.595	Remote Similarity	NPD7503	Approved
0.5946	Remote Similarity	NPD6052	Approved
0.5941	Remote Similarity	NPD5329	Approved
0.5934	Remote Similarity	NPD229	Approved
0.5926	Remote Similarity	NPD4755	Approved
0.5922	Remote Similarity	NPD5208	Approved
0.592	Remote Similarity	NPD6033	Approved
0.5905	Remote Similarity	NPD6050	Approved
0.5905	Remote Similarity	NPD5693	Phase 1
0.5904	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7115	Discovery
0.5877	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7638	Approved
0.5868	Remote Similarity	NPD6319	Approved
0.5859	Remote Similarity	NPD5369	Approved
0.5859	Remote Similarity	NPD4692	Approved
0.5859	Remote Similarity	NPD4139	Approved
0.5843	Remote Similarity	NPD7909	Approved
0.5842	Remote Similarity	NPD4197	Approved
0.5833	Remote Similarity	NPD6335	Approved
0.5818	Remote Similarity	NPD7640	Approved
0.5818	Remote Similarity	NPD4700	Approved
0.5818	Remote Similarity	NPD5285	Approved
0.5818	Remote Similarity	NPD4696	Approved
0.5818	Remote Similarity	NPD5286	Approved
0.5818	Remote Similarity	NPD7639	Approved
0.5818	Remote Similarity	NPD8418	Phase 2
0.5812	Remote Similarity	NPD6053	Discontinued
0.581	Remote Similarity	NPD5692	Phase 3
0.58	Remote Similarity	NPD3667	Approved
0.58	Remote Similarity	NPD6435	Approved
0.5798	Remote Similarity	NPD6274	Approved
0.5785	Remote Similarity	NPD7100	Approved
0.5785	Remote Similarity	NPD7101	Approved
0.5784	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.578	Remote Similarity	NPD7902	Approved
0.5766	Remote Similarity	NPD5223	Approved
0.5755	Remote Similarity	NPD5694	Approved
0.575	Remote Similarity	NPD6317	Approved
0.5743	Remote Similarity	NPD5362	Discontinued
0.5728	Remote Similarity	NPD5205	Approved
0.5728	Remote Similarity	NPD3618	Phase 1
0.5728	Remote Similarity	NPD4138	Approved
0.5728	Remote Similarity	NPD4688	Approved
0.5728	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD4689	Approved
0.5728	Remote Similarity	NPD4693	Phase 3
0.5728	Remote Similarity	NPD4690	Approved
0.5726	Remote Similarity	NPD8328	Phase 3
0.5726	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD8139	Approved
0.5714	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8086	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