NPASS Compound

Structure

CID198549 OpenBabel06191715582D 35 39 0 0 1 0 0 0 0 0999 V2000 4.3102 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3791 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7068 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8017 -3.3793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4366 -1.7168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6378 0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8017 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3821 -3.4686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9754 -4.3821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6378 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4311 -1.8213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4828 -0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4740 -1.4483 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5430 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7068 0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9655 -2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6390 -2.7995 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6378 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9655 0.9655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4366 -1.7168 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8017 -1.4483 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7730 -3.2995 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4740 -0.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8017 -0.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9655 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5430 -2.4138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5430 1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -3.3793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9809 -4.2776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7068 -0.9655 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 0.1294 1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9655 -1.9310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0298 -2.6303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 6 7 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 9 2 0 0 0 0 9 30 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 18 1 0 0 0 0 12 25 1 0 0 0 0 12 31 1 0 0 0 0 13 32 1 0 0 0 0 14 24 1 6 0 0 0 15 27 2 0 0 0 0 15 31 1 0 0 0 0 16 28 2 0 0 0 0 16 33 1 0 0 0 0 17 29 2 0 0 0 0 17 34 1 0 0 0 0 18 8 1 6 0 0 0 18 23 1 0 0 0 0 19 24 1 6 0 0 0 19 25 1 0 0 0 0 20 26 1 6 0 0 0 20 33 1 0 0 0 0 21 11 1 1 0 0 0 21 24 1 0 0 0 0 21 35 1 0 0 0 0 22 25 1 6 0 0 0 22 34 1 0 0 0 0 23 30 1 6 0 0 0 23 35 1 0 0 0 0 24 5 1 1 0 0 0 25 26 1 1 0 0 0 26 13 1 1 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.24
Volume:	484.036
LogP:	2.382
LogD:	2.33
LogS:	-4.51
# Rotatable Bonds:	8
TPSA:	109.89
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	5.848
Fsp3:	0.808
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.086
MDCK Permeability:	6.546181975863874e-05
Pgp-inhibitor:	0.93
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.069
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.742
Plasma Protein Binding (PPB):	37.1035270690918%
Volume Distribution (VD):	1.456
Pgp-substrate:	39.136375427246094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.208
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.636
CYP3A4-substrate:	0.431

ADMET: Excretion

Clearance (CL):	3.391
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.773
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.822
AMES Toxicity:	0.872
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.854
Skin Sensitization:	0.948
Carcinogencity:	0.876
Eye Corrosion:	0.01
Eye Irritation:	0.125
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC198549

Natural Product ID:	NPC198549
*Common Name:**	Caryoptin
IUPAC Name:	[(3R,4R,4aR,5S,7R,8S,8aR)-8-[(3aS,5S,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-3,5-diacetyloxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
Synonyms:
Standard InCHIKey:	QVORLEZTALRJNW-SHZKAIFQSA-N
Standard InCHI:	InChI=1S/C26H36O9/c1-14-10-22(34-17(4)29)25(12-31-15(2)27)19(6-7-20(33-16(3)28)26(25)13-32-26)24(14,5)21-11-18-8-9-30-23(18)35-21/h8-9,14,18-23H,6-7,10-13H2,1-5H3/t14-,18-,19-,20-,21+,22+,23+,24+,25+,26-/m1/s1
SMILES:	CC(=O)OC[C@@]12[C@@H](OC(=O)C)C[C@H]([C@]([C@H]1CC[C@H]([C@@]12CO1)OC(=O)C)(C)[C@H]1O[C@H]2[C@@H](C1)C=CO2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269919
PubChem CID:	442010
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO26560	Caryopteris divaricata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)92000-3]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26560	Caryopteris divaricata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26560	Caryopteris divaricata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Others	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	72.51	%	PMID[454035]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	84.95	%	PMID[454035]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	-5.31	%	PMID[454035]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	44.46	%	PMID[454035]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	34.37	%	PMID[454035]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	-10.03	%	PMID[454035]

☑ 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 NPC198549 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	241
0.1-0.2	2094
0.2-0.3	6482
0.3-0.4	14576
0.4-0.5	8427
0.5-0.6	6529
0.6-0.7	4015
0.7-0.8	324
0.8-0.85	3
0.85-0.9	1
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC113976
0.9556	High Similarity	NPC12297
0.9278	High Similarity	NPC291414
0.9	High Similarity	NPC305939
0.8911	High Similarity	NPC86217
0.828	Intermediate Similarity	NPC474008
0.8261	Intermediate Similarity	NPC471367
0.8105	Intermediate Similarity	NPC470872
0.8085	Intermediate Similarity	NPC471369
0.8022	Intermediate Similarity	NPC471217
0.8022	Intermediate Similarity	NPC471216
0.7959	Intermediate Similarity	NPC163902
0.7941	Intermediate Similarity	NPC119467
0.7941	Intermediate Similarity	NPC475767
0.7935	Intermediate Similarity	NPC71541
0.7917	Intermediate Similarity	NPC263079
0.79	Intermediate Similarity	NPC171598
0.7895	Intermediate Similarity	NPC471368
0.7843	Intermediate Similarity	NPC317019
0.78	Intermediate Similarity	NPC471362
0.78	Intermediate Similarity	NPC471372
0.78	Intermediate Similarity	NPC472189
0.7789	Intermediate Similarity	NPC235402
0.7788	Intermediate Similarity	NPC120009
0.7778	Intermediate Similarity	NPC475307
0.7757	Intermediate Similarity	NPC206618
0.7755	Intermediate Similarity	NPC471371
0.7755	Intermediate Similarity	NPC471370
0.7745	Intermediate Similarity	NPC318917
0.7745	Intermediate Similarity	NPC472186
0.7745	Intermediate Similarity	NPC476800
0.7745	Intermediate Similarity	NPC471366
0.7745	Intermediate Similarity	NPC157739
0.7714	Intermediate Similarity	NPC470062
0.7714	Intermediate Similarity	NPC470058
0.7714	Intermediate Similarity	NPC85593
0.7714	Intermediate Similarity	NPC470043
0.7714	Intermediate Similarity	NPC470060
0.7714	Intermediate Similarity	NPC470059
0.7714	Intermediate Similarity	NPC470064
0.7714	Intermediate Similarity	NPC470061
0.7714	Intermediate Similarity	NPC470057
0.7714	Intermediate Similarity	NPC31430
0.767	Intermediate Similarity	NPC324598
0.767	Intermediate Similarity	NPC473545
0.767	Intermediate Similarity	NPC473204
0.767	Intermediate Similarity	NPC472187
0.7664	Intermediate Similarity	NPC128795
0.7664	Intermediate Similarity	NPC38948
0.7664	Intermediate Similarity	NPC48548
0.7664	Intermediate Similarity	NPC135015
0.7664	Intermediate Similarity	NPC217921
0.7658	Intermediate Similarity	NPC243981
0.7647	Intermediate Similarity	NPC471770
0.7647	Intermediate Similarity	NPC473555
0.7647	Intermediate Similarity	NPC97867
0.7647	Intermediate Similarity	NPC278939
0.7647	Intermediate Similarity	NPC472188
0.7624	Intermediate Similarity	NPC230347
0.7624	Intermediate Similarity	NPC286612
0.7624	Intermediate Similarity	NPC275310
0.7619	Intermediate Similarity	NPC474575
0.7593	Intermediate Similarity	NPC316974
0.7593	Intermediate Similarity	NPC40728
0.7573	Intermediate Similarity	NPC477928
0.757	Intermediate Similarity	NPC125423
0.757	Intermediate Similarity	NPC88013
0.757	Intermediate Similarity	NPC475074
0.7551	Intermediate Similarity	NPC144069
0.7549	Intermediate Similarity	NPC94905
0.7549	Intermediate Similarity	NPC8954
0.7525	Intermediate Similarity	NPC140277
0.7525	Intermediate Similarity	NPC211238
0.7523	Intermediate Similarity	NPC127153
0.75	Intermediate Similarity	NPC18953
0.75	Intermediate Similarity	NPC91251
0.75	Intermediate Similarity	NPC311223
0.7478	Intermediate Similarity	NPC204731
0.7477	Intermediate Similarity	NPC470055
0.7477	Intermediate Similarity	NPC51719
0.7477	Intermediate Similarity	NPC473199
0.7477	Intermediate Similarity	NPC470767
0.7477	Intermediate Similarity	NPC165405
0.7477	Intermediate Similarity	NPC144068
0.7477	Intermediate Similarity	NPC470763
0.7477	Intermediate Similarity	NPC239961
0.7477	Intermediate Similarity	NPC470056
0.7476	Intermediate Similarity	NPC266417
0.7475	Intermediate Similarity	NPC161560
0.7455	Intermediate Similarity	NPC17791
0.7453	Intermediate Similarity	NPC127933
0.7453	Intermediate Similarity	NPC475889
0.7453	Intermediate Similarity	NPC7644
0.7453	Intermediate Similarity	NPC7613
0.7449	Intermediate Similarity	NPC213658
0.7449	Intermediate Similarity	NPC264546
0.7449	Intermediate Similarity	NPC45833
0.7449	Intermediate Similarity	NPC110365
0.7449	Intermediate Similarity	NPC62202
0.7431	Intermediate Similarity	NPC51925
0.7431	Intermediate Similarity	NPC43976
0.7431	Intermediate Similarity	NPC154085
0.7431	Intermediate Similarity	NPC125361
0.7431	Intermediate Similarity	NPC296761
0.7426	Intermediate Similarity	NPC474835
0.7407	Intermediate Similarity	NPC293512
0.7407	Intermediate Similarity	NPC470169
0.7407	Intermediate Similarity	NPC470170
0.7404	Intermediate Similarity	NPC216260
0.7404	Intermediate Similarity	NPC5358
0.74	Intermediate Similarity	NPC474249
0.74	Intermediate Similarity	NPC261990
0.7396	Intermediate Similarity	NPC127917
0.7391	Intermediate Similarity	NPC241192
0.7387	Intermediate Similarity	NPC222834
0.7387	Intermediate Similarity	NPC470025
0.7387	Intermediate Similarity	NPC317460
0.7387	Intermediate Similarity	NPC473125
0.7387	Intermediate Similarity	NPC328074
0.7387	Intermediate Similarity	NPC321272
0.7383	Intermediate Similarity	NPC264867
0.7383	Intermediate Similarity	NPC81567
0.7383	Intermediate Similarity	NPC201880
0.7383	Intermediate Similarity	NPC473207
0.7383	Intermediate Similarity	NPC470321
0.7379	Intermediate Similarity	NPC194132
0.7379	Intermediate Similarity	NPC209297
0.7379	Intermediate Similarity	NPC475380
0.7374	Intermediate Similarity	NPC470260
0.7374	Intermediate Similarity	NPC221993
0.7374	Intermediate Similarity	NPC75443
0.7374	Intermediate Similarity	NPC106332
0.7368	Intermediate Similarity	NPC472080
0.7364	Intermediate Similarity	NPC177047
0.7364	Intermediate Similarity	NPC119550
0.7364	Intermediate Similarity	NPC101450
0.7364	Intermediate Similarity	NPC316708
0.7358	Intermediate Similarity	NPC154452
0.7358	Intermediate Similarity	NPC238397
0.7358	Intermediate Similarity	NPC471363
0.7358	Intermediate Similarity	NPC472815
0.7358	Intermediate Similarity	NPC470571
0.7355	Intermediate Similarity	NPC42206
0.7353	Intermediate Similarity	NPC178949
0.7353	Intermediate Similarity	NPC96736
0.7347	Intermediate Similarity	NPC471411
0.7347	Intermediate Similarity	NPC214315
0.7347	Intermediate Similarity	NPC471410
0.7345	Intermediate Similarity	NPC212660
0.7339	Intermediate Similarity	NPC472988
0.7339	Intermediate Similarity	NPC181994
0.7339	Intermediate Similarity	NPC473517
0.7339	Intermediate Similarity	NPC38217
0.7333	Intermediate Similarity	NPC146188
0.7327	Intermediate Similarity	NPC120539
0.7327	Intermediate Similarity	NPC8729
0.7321	Intermediate Similarity	NPC40133
0.7321	Intermediate Similarity	NPC470027
0.7321	Intermediate Similarity	NPC49413
0.7321	Intermediate Similarity	NPC290608
0.7321	Intermediate Similarity	NPC44298
0.7321	Intermediate Similarity	NPC473128
0.7315	Intermediate Similarity	NPC218158
0.7308	Intermediate Similarity	NPC311241
0.7308	Intermediate Similarity	NPC475446
0.7308	Intermediate Similarity	NPC100912
0.7304	Intermediate Similarity	NPC153085
0.7304	Intermediate Similarity	NPC268326
0.7304	Intermediate Similarity	NPC161065
0.73	Intermediate Similarity	NPC170633
0.7297	Intermediate Similarity	NPC470026
0.7297	Intermediate Similarity	NPC272242
0.7297	Intermediate Similarity	NPC65167
0.729	Intermediate Similarity	NPC165608
0.729	Intermediate Similarity	NPC281378
0.729	Intermediate Similarity	NPC213190
0.729	Intermediate Similarity	NPC134270
0.7281	Intermediate Similarity	NPC290693
0.7281	Intermediate Similarity	NPC152615
0.7281	Intermediate Similarity	NPC203862
0.7273	Intermediate Similarity	NPC473570
0.7265	Intermediate Similarity	NPC115349
0.7264	Intermediate Similarity	NPC21064
0.7264	Intermediate Similarity	NPC472554
0.7264	Intermediate Similarity	NPC121072
0.7263	Intermediate Similarity	NPC472943
0.7263	Intermediate Similarity	NPC475456
0.7263	Intermediate Similarity	NPC472951
0.7255	Intermediate Similarity	NPC246860
0.7253	Intermediate Similarity	NPC12680
0.7248	Intermediate Similarity	NPC234160
0.7248	Intermediate Similarity	NPC184512
0.7248	Intermediate Similarity	NPC122816
0.7248	Intermediate Similarity	NPC109376
0.7248	Intermediate Similarity	NPC471205
0.7245	Intermediate Similarity	NPC476725
0.7241	Intermediate Similarity	NPC151616
0.7238	Intermediate Similarity	NPC72647
0.7238	Intermediate Similarity	NPC107806
0.7238	Intermediate Similarity	NPC312325

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 NPC198549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	2503
0.2-0.3	4070
0.3-0.4	1629
0.4-0.5	431
0.5-0.6	271
0.6-0.7	50
0.7-0.8	0
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
0.7155	Intermediate Similarity	NPD7516	Approved
0.7069	Intermediate Similarity	NPD7327	Approved
0.7069	Intermediate Similarity	NPD7328	Approved
0.7034	Intermediate Similarity	NPD8033	Approved
0.6949	Remote Similarity	NPD8294	Approved
0.6949	Remote Similarity	NPD8377	Approved
0.6891	Remote Similarity	NPD8379	Approved
0.6891	Remote Similarity	NPD8296	Approved
0.6891	Remote Similarity	NPD7503	Approved
0.6891	Remote Similarity	NPD8335	Approved
0.6891	Remote Similarity	NPD8378	Approved
0.6891	Remote Similarity	NPD8380	Approved
0.6726	Remote Similarity	NPD6686	Approved
0.6724	Remote Similarity	NPD8133	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7507	Approved
0.6637	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7736	Approved
0.6557	Remote Similarity	NPD6370	Approved
0.6545	Remote Similarity	NPD6648	Approved
0.6508	Remote Similarity	NPD7319	Approved
0.6486	Remote Similarity	NPD5344	Discontinued
0.648	Remote Similarity	NPD8293	Discontinued
0.6466	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7492	Approved
0.6435	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3168	Discontinued
0.64	Remote Similarity	NPD6616	Approved
0.6393	Remote Similarity	NPD6054	Approved
0.6379	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7078	Approved
0.6348	Remote Similarity	NPD6412	Phase 2
0.6296	Remote Similarity	NPD8171	Discontinued
0.6281	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6059	Approved
0.624	Remote Similarity	NPD8328	Phase 3
0.6218	Remote Similarity	NPD6882	Approved
0.6214	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD3669	Approved
0.621	Remote Similarity	NPD6016	Approved
0.621	Remote Similarity	NPD6015	Approved
0.6161	Remote Similarity	NPD7638	Approved
0.6161	Remote Similarity	NPD4225	Approved
0.616	Remote Similarity	NPD5988	Approved
0.6148	Remote Similarity	NPD6009	Approved
0.6146	Remote Similarity	NPD2686	Approved
0.6146	Remote Similarity	NPD2254	Approved
0.6146	Remote Similarity	NPD2687	Approved
0.6111	Remote Similarity	NPD6067	Discontinued
0.6106	Remote Similarity	NPD7640	Approved
0.6106	Remote Similarity	NPD7639	Approved
0.6083	Remote Similarity	NPD8297	Approved
0.608	Remote Similarity	NPD8516	Approved
0.608	Remote Similarity	NPD8515	Approved
0.608	Remote Similarity	NPD8517	Approved
0.608	Remote Similarity	NPD8513	Phase 3
0.6055	Remote Similarity	NPD8035	Phase 2
0.6055	Remote Similarity	NPD8034	Phase 2
0.6044	Remote Similarity	NPD1145	Discontinued
0.6036	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD1779	Approved
0.6019	Remote Similarity	NPD1780	Approved
0.6016	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5981	Remote Similarity	NPD7524	Approved
0.5979	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6921	Approved
0.5946	Remote Similarity	NPD7900	Approved
0.5946	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7525	Registered
0.5922	Remote Similarity	NPD6928	Phase 2
0.5902	Remote Similarity	NPD4632	Approved
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD7320	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.5872	Remote Similarity	NPD6051	Approved
0.5868	Remote Similarity	NPD6650	Approved
0.5868	Remote Similarity	NPD6649	Approved
0.5862	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7604	Phase 2
0.5849	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6402	Approved
0.5847	Remote Similarity	NPD7128	Approved
0.5847	Remote Similarity	NPD5357	Phase 1
0.5847	Remote Similarity	NPD6675	Approved
0.5847	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD4250	Approved
0.5833	Remote Similarity	NPD4251	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5818	Remote Similarity	NPD7838	Discovery
0.5804	Remote Similarity	NPD7748	Approved
0.5804	Remote Similarity	NPD5282	Discontinued
0.5802	Remote Similarity	NPD6033	Approved
0.58	Remote Similarity	NPD1810	Approved
0.58	Remote Similarity	NPD1811	Approved
0.5798	Remote Similarity	NPD5697	Approved
0.5794	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7902	Approved
0.5785	Remote Similarity	NPD7290	Approved
0.5785	Remote Similarity	NPD7102	Approved
0.5785	Remote Similarity	NPD6883	Approved
0.578	Remote Similarity	NPD6903	Approved
0.5776	Remote Similarity	NPD1700	Approved
0.5775	Remote Similarity	NPD7625	Phase 1
0.5766	Remote Similarity	NPD7637	Suspended
0.5755	Remote Similarity	NPD6695	Phase 3
0.5741	Remote Similarity	NPD4249	Approved
0.5741	Remote Similarity	NPD7521	Approved
0.5741	Remote Similarity	NPD5330	Approved
0.5741	Remote Similarity	NPD7334	Approved
0.5741	Remote Similarity	NPD6409	Approved
0.5741	Remote Similarity	NPD7146	Approved
0.5741	Remote Similarity	NPD6684	Approved
0.5739	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6847	Approved
0.5738	Remote Similarity	NPD6617	Approved
0.5738	Remote Similarity	NPD8130	Phase 1
0.5738	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6869	Approved
0.5703	Remote Similarity	NPD5983	Phase 2
0.5702	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD6014	Approved
0.5702	Remote Similarity	NPD6012	Approved
0.5701	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD3573	Approved
0.5676	Remote Similarity	NPD46	Approved
0.5676	Remote Similarity	NPD6698	Approved
0.5673	Remote Similarity	NPD7645	Phase 2
0.5667	Remote Similarity	NPD5701	Approved
0.5664	Remote Similarity	NPD6001	Approved
0.566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD6336	Discontinued
0.5636	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD5737	Approved
0.5636	Remote Similarity	NPD6672	Approved
0.563	Remote Similarity	NPD8338	Approved
0.563	Remote Similarity	NPD8449	Approved
0.5625	Remote Similarity	NPD7515	Phase 2
0.562	Remote Similarity	NPD6011	Approved
0.5606	Remote Similarity	NPD8074	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