NPASS Compound

Structure

NPC12933 OpenBabel07101719142D 35 39 0 0 1 0 0 0 0 0999 V2000 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3096 5.2471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5175 4.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5665 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9266 2.8838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9131 -1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3308 -1.0181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8973 5.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 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 28 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 17 28 1 0 0 0 0 17 29 1 0 0 0 0 18 1 1 1 0 0 0 18 19 1 0 0 0 0 19 27 1 6 0 0 0 20 25 1 0 0 0 0 20 28 1 6 0 0 0 21 29 1 1 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 26 1 0 0 0 0 23 32 1 1 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 35 1 0 0 0 0 27 30 1 6 0 0 0 28 29 1 1 0 0 0 29 16 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	525.968
LogP:	3.969
LogD:	3.968
LogS:	-3.429
# Rotatable Bonds:	6
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	5.773
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.414
MDCK Permeability:	1.4674506928713527e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	93.38433837890625%
Volume Distribution (VD):	0.737
Pgp-substrate:	2.7445645332336426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.271
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	2.158
Half-life (T1/2):	0.339

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.34
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.923
Carcinogencity:	0.015
Eye Corrosion:	0.024
Eye Irritation:	0.309
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC12933

Natural Product ID:	NPC12933
*Common Name:**	Caloncobic Acid B
IUPAC Name:	n.a.
Synonyms:	caloncobic acid B
Standard InCHIKey:	WDJQHANSLSJHNN-XEPWAXDFSA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-18(7-10-23(32)26(4,5)35)19-11-14-30(24(33)34)21-9-8-20-25(2,3)22(31)12-13-28(20)17-29(21,28)16-15-27(19,30)6/h18-23,31-32,35H,7-17H2,1-6H3,(H,33,34)/t18-,19-,20+,21-,22+,23-,27-,28-,29+,30+/m1/s1
SMILES:	C[C@H](CC[C@H](C(C)(C)O)O)[C@H]1CC[C@]2([C@@H]3CC[C@H]4C(C)(C)[C@H](CC[C@]54C[C@@]35CC[C@]12C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2035569
PubChem CID:	57408765
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO13364	Caloncoba glauca	Species	Achariaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22360639]
NPO13364	Caloncoba glauca	Species	Achariaceae	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
IC50	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	IC50	=	72.0	nM	PMID[483663]
NPT4862	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	IC50	=	13.0	nM	PMID[483663]
NPT1138	Individual Protein	11-beta-hydroxysteroid dehydrogenase 2	Homo sapiens	IC50	=	400.0	nM	PMID[483663]
NPT4861	Individual Protein	11-beta-hydroxysteroid dehydrogenase 2	Mus musculus	IC50	>	100000.0	nM	PMID[483663]

☑ 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 NPC12933 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	359
0.1-0.2	3135
0.2-0.3	12469
0.3-0.4	11269
0.4-0.5	5758
0.5-0.6	5256
0.6-0.7	3429
0.7-0.8	833
0.8-0.85	136
0.85-0.9	38
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC4209
0.9211	High Similarity	NPC317913
0.9211	High Similarity	NPC207010
0.92	High Similarity	NPC212733
0.9114	High Similarity	NPC121121
0.9091	High Similarity	NPC224802
0.9091	High Similarity	NPC324700
0.9091	High Similarity	NPC171426
0.9091	High Similarity	NPC34046
0.9091	High Similarity	NPC80089
0.9067	High Similarity	NPC167702
0.9067	High Similarity	NPC280026
0.9036	High Similarity	NPC24705
0.9036	High Similarity	NPC56962
0.8974	High Similarity	NPC201276
0.8974	High Similarity	NPC320144
0.8974	High Similarity	NPC80891
0.8961	High Similarity	NPC298168
0.8961	High Similarity	NPC180199
0.8961	High Similarity	NPC475031
0.8961	High Similarity	NPC143133
0.8961	High Similarity	NPC264602
0.8961	High Similarity	NPC477919
0.8947	High Similarity	NPC273366
0.8902	High Similarity	NPC472272
0.8861	High Similarity	NPC477851
0.8846	High Similarity	NPC185465
0.8846	High Similarity	NPC476732
0.8846	High Similarity	NPC199965
0.875	High Similarity	NPC58631
0.8684	High Similarity	NPC232112
0.8675	High Similarity	NPC302111
0.8667	High Similarity	NPC477850
0.8659	High Similarity	NPC319909
0.8642	High Similarity	NPC289486
0.8642	High Similarity	NPC61107
0.8642	High Similarity	NPC30583
0.8625	High Similarity	NPC261616
0.8608	High Similarity	NPC329117
0.8571	High Similarity	NPC202937
0.8553	High Similarity	NPC151018
0.8553	High Similarity	NPC156277
0.8553	High Similarity	NPC320549
0.8553	High Similarity	NPC58057
0.8537	High Similarity	NPC259173
0.8533	High Similarity	NPC299948
0.8533	High Similarity	NPC469941
0.8533	High Similarity	NPC470830
0.8533	High Similarity	NPC196197
0.8533	High Similarity	NPC319671
0.8533	High Similarity	NPC476734
0.8533	High Similarity	NPC252032
0.8533	High Similarity	NPC241085
0.8519	High Similarity	NPC469745
0.8481	Intermediate Similarity	NPC23884
0.8462	Intermediate Similarity	NPC97534
0.8462	Intermediate Similarity	NPC195155
0.8462	Intermediate Similarity	NPC174964
0.8434	Intermediate Similarity	NPC471044
0.8434	Intermediate Similarity	NPC473336
0.8421	Intermediate Similarity	NPC477929
0.8415	Intermediate Similarity	NPC477935
0.8415	Intermediate Similarity	NPC317066
0.8395	Intermediate Similarity	NPC470609
0.8395	Intermediate Similarity	NPC472853
0.8372	Intermediate Similarity	NPC220498
0.8354	Intermediate Similarity	NPC5767
0.8354	Intermediate Similarity	NPC472487
0.8354	Intermediate Similarity	NPC475742
0.8354	Intermediate Similarity	NPC472486
0.8333	Intermediate Similarity	NPC254340
0.8333	Intermediate Similarity	NPC472854
0.8333	Intermediate Similarity	NPC477930
0.8315	Intermediate Similarity	NPC470031
0.8313	Intermediate Similarity	NPC472744
0.8312	Intermediate Similarity	NPC469940
0.8312	Intermediate Similarity	NPC89310
0.8295	Intermediate Similarity	NPC472232
0.8295	Intermediate Similarity	NPC472231
0.8289	Intermediate Similarity	NPC327728
0.8289	Intermediate Similarity	NPC213178
0.8289	Intermediate Similarity	NPC474962
0.8289	Intermediate Similarity	NPC107919
0.8289	Intermediate Similarity	NPC6120
0.8289	Intermediate Similarity	NPC131892
0.8276	Intermediate Similarity	NPC475056
0.8276	Intermediate Similarity	NPC77756
0.8267	Intermediate Similarity	NPC130459
0.8267	Intermediate Similarity	NPC474221
0.8267	Intermediate Similarity	NPC478180
0.8256	Intermediate Similarity	NPC146937
0.825	Intermediate Similarity	NPC474404
0.825	Intermediate Similarity	NPC221420
0.825	Intermediate Similarity	NPC171658
0.8235	Intermediate Similarity	NPC475007
0.8235	Intermediate Similarity	NPC476727
0.8235	Intermediate Similarity	NPC476726
0.8235	Intermediate Similarity	NPC2783
0.8235	Intermediate Similarity	NPC80700
0.8235	Intermediate Similarity	NPC92139
0.8228	Intermediate Similarity	NPC472311
0.8228	Intermediate Similarity	NPC24014
0.8228	Intermediate Similarity	NPC21220
0.8228	Intermediate Similarity	NPC27349
0.8228	Intermediate Similarity	NPC125767
0.8214	Intermediate Similarity	NPC474996
0.8205	Intermediate Similarity	NPC472341
0.8205	Intermediate Similarity	NPC81759
0.8205	Intermediate Similarity	NPC473238
0.8193	Intermediate Similarity	NPC164289
0.8193	Intermediate Similarity	NPC268040
0.8193	Intermediate Similarity	NPC154043
0.8193	Intermediate Similarity	NPC202688
0.8193	Intermediate Similarity	NPC100366
0.8193	Intermediate Similarity	NPC242771
0.8193	Intermediate Similarity	NPC311642
0.8193	Intermediate Similarity	NPC477936
0.8193	Intermediate Similarity	NPC60018
0.8182	Intermediate Similarity	NPC52756
0.8148	Intermediate Similarity	NPC472608
0.814	Intermediate Similarity	NPC263802
0.814	Intermediate Similarity	NPC252714
0.814	Intermediate Similarity	NPC264005
0.814	Intermediate Similarity	NPC269360
0.814	Intermediate Similarity	NPC33768
0.8133	Intermediate Similarity	NPC268736
0.8133	Intermediate Similarity	NPC477931
0.8133	Intermediate Similarity	NPC42060
0.8125	Intermediate Similarity	NPC477933
0.8125	Intermediate Similarity	NPC477932
0.8118	Intermediate Similarity	NPC264317
0.8118	Intermediate Similarity	NPC131350
0.8118	Intermediate Similarity	NPC294438
0.8095	Intermediate Similarity	NPC111582
0.8095	Intermediate Similarity	NPC327451
0.8095	Intermediate Similarity	NPC477285
0.809	Intermediate Similarity	NPC291373
0.8077	Intermediate Similarity	NPC473267
0.8072	Intermediate Similarity	NPC77311
0.8072	Intermediate Similarity	NPC476071
0.8072	Intermediate Similarity	NPC280781
0.8072	Intermediate Similarity	NPC190940
0.8072	Intermediate Similarity	NPC48756
0.8052	Intermediate Similarity	NPC64466
0.8049	Intermediate Similarity	NPC220379
0.8046	Intermediate Similarity	NPC16377
0.8046	Intermediate Similarity	NPC476379
0.8046	Intermediate Similarity	NPC474719
0.8026	Intermediate Similarity	NPC475884
0.8026	Intermediate Similarity	NPC41542
0.8026	Intermediate Similarity	NPC473230
0.8025	Intermediate Similarity	NPC477918
0.8025	Intermediate Similarity	NPC212453
0.8023	Intermediate Similarity	NPC472745
0.8023	Intermediate Similarity	NPC474448
0.8023	Intermediate Similarity	NPC70661
0.8023	Intermediate Similarity	NPC12774
0.8022	Intermediate Similarity	NPC116683
0.8	Intermediate Similarity	NPC41577
0.8	Intermediate Similarity	NPC159789
0.8	Intermediate Similarity	NPC474380
0.8	Intermediate Similarity	NPC470423
0.8	Intermediate Similarity	NPC477934
0.8	Intermediate Similarity	NPC277399
0.8	Intermediate Similarity	NPC230047
0.8	Intermediate Similarity	NPC179858
0.8	Intermediate Similarity	NPC186851
0.8	Intermediate Similarity	NPC473276
0.8	Intermediate Similarity	NPC19311
0.8	Intermediate Similarity	NPC50438
0.7978	Intermediate Similarity	NPC189520
0.7976	Intermediate Similarity	NPC102156
0.7976	Intermediate Similarity	NPC477286
0.7976	Intermediate Similarity	NPC328007
0.7976	Intermediate Similarity	NPC286719
0.7976	Intermediate Similarity	NPC13494
0.7976	Intermediate Similarity	NPC148740
0.7975	Intermediate Similarity	NPC153719
0.7975	Intermediate Similarity	NPC310766
0.7955	Intermediate Similarity	NPC213832
0.7955	Intermediate Similarity	NPC57954
0.7949	Intermediate Similarity	NPC231945
0.7949	Intermediate Similarity	NPC108131
0.7931	Intermediate Similarity	NPC239938
0.7927	Intermediate Similarity	NPC26029
0.7927	Intermediate Similarity	NPC31031
0.7927	Intermediate Similarity	NPC471045
0.7927	Intermediate Similarity	NPC147993
0.7927	Intermediate Similarity	NPC478128
0.7927	Intermediate Similarity	NPC243594
0.7912	Intermediate Similarity	NPC263135
0.7912	Intermediate Similarity	NPC288906
0.7912	Intermediate Similarity	NPC266431
0.7907	Intermediate Similarity	NPC76518
0.7907	Intermediate Similarity	NPC266651
0.7901	Intermediate Similarity	NPC471046
0.7882	Intermediate Similarity	NPC217559
0.7882	Intermediate Similarity	NPC292458
0.7882	Intermediate Similarity	NPC268578
0.7882	Intermediate Similarity	NPC471037

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 NPC12933 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	3424
0.2-0.3	3591
0.3-0.4	1074
0.4-0.5	287
0.5-0.6	224
0.6-0.7	134
0.7-0.8	16
0.8-0.85	9
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD6117	Approved
0.9211	High Similarity	NPD6116	Phase 1
0.9091	High Similarity	NPD6114	Approved
0.9091	High Similarity	NPD6697	Approved
0.9091	High Similarity	NPD6118	Approved
0.9091	High Similarity	NPD6115	Approved
0.9067	High Similarity	NPD6113	Clinical (unspecified phase)
0.8553	High Similarity	NPD4809	Clinical (unspecified phase)
0.8553	High Similarity	NPD4808	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD5360	Phase 3
0.8158	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6081	Approved
0.8	Intermediate Similarity	NPD3703	Phase 2
0.7949	Intermediate Similarity	NPD4789	Approved
0.7949	Intermediate Similarity	NPD4245	Approved
0.7949	Intermediate Similarity	NPD4244	Approved
0.7895	Intermediate Similarity	NPD4224	Phase 2
0.7821	Intermediate Similarity	NPD3698	Phase 2
0.7778	Intermediate Similarity	NPD3702	Approved
0.7763	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4758	Discontinued
0.7625	Intermediate Similarity	NPD5777	Approved
0.7582	Intermediate Similarity	NPD8034	Phase 2
0.7582	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD5364	Discontinued
0.75	Intermediate Similarity	NPD3671	Phase 1
0.7284	Intermediate Similarity	NPD4787	Phase 1
0.7216	Intermediate Similarity	NPD8418	Phase 2
0.7079	Intermediate Similarity	NPD4788	Approved
0.7021	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD4786	Approved
0.6989	Remote Similarity	NPD5328	Approved
0.6947	Remote Similarity	NPD6399	Phase 3
0.6932	Remote Similarity	NPD7525	Registered
0.6883	Remote Similarity	NPD3198	Approved
0.6863	Remote Similarity	NPD7128	Approved
0.6863	Remote Similarity	NPD5739	Approved
0.6863	Remote Similarity	NPD6402	Approved
0.6863	Remote Similarity	NPD6675	Approved
0.6848	Remote Similarity	NPD3618	Phase 1
0.6842	Remote Similarity	NPD6079	Approved
0.6778	Remote Similarity	NPD3667	Approved
0.6771	Remote Similarity	NPD4202	Approved
0.6768	Remote Similarity	NPD7638	Approved
0.6765	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6881	Approved
0.6731	Remote Similarity	NPD7320	Approved
0.6731	Remote Similarity	NPD6899	Approved
0.6701	Remote Similarity	NPD7748	Approved
0.67	Remote Similarity	NPD7640	Approved
0.67	Remote Similarity	NPD7639	Approved
0.6697	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD5701	Approved
0.6635	Remote Similarity	NPD5697	Approved
0.6633	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7290	Approved
0.6604	Remote Similarity	NPD7102	Approved
0.6604	Remote Similarity	NPD6883	Approved
0.6574	Remote Similarity	NPD8133	Approved
0.6574	Remote Similarity	NPD4632	Approved
0.6571	Remote Similarity	NPD6011	Approved
0.6569	Remote Similarity	NPD7632	Discontinued
0.6566	Remote Similarity	NPD5222	Approved
0.6566	Remote Similarity	NPD4697	Phase 3
0.6566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5221	Approved
0.6556	Remote Similarity	NPD6928	Phase 2
0.6543	Remote Similarity	NPD7909	Approved
0.6542	Remote Similarity	NPD6650	Approved
0.6542	Remote Similarity	NPD8130	Phase 1
0.6542	Remote Similarity	NPD6869	Approved
0.6542	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6617	Approved
0.6542	Remote Similarity	NPD6847	Approved
0.6542	Remote Similarity	NPD6649	Approved
0.6535	Remote Similarity	NPD4696	Approved
0.6535	Remote Similarity	NPD5286	Approved
0.6535	Remote Similarity	NPD5285	Approved
0.6535	Remote Similarity	NPD4700	Approved
0.6509	Remote Similarity	NPD6013	Approved
0.6509	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6014	Approved
0.6509	Remote Similarity	NPD6012	Approved
0.65	Remote Similarity	NPD7902	Approved
0.65	Remote Similarity	NPD5173	Approved
0.6481	Remote Similarity	NPD6882	Approved
0.6471	Remote Similarity	NPD1700	Approved
0.6471	Remote Similarity	NPD5223	Approved
0.6458	Remote Similarity	NPD4753	Phase 2
0.6455	Remote Similarity	NPD6940	Discontinued
0.6452	Remote Similarity	NPD3666	Approved
0.6452	Remote Similarity	NPD3133	Approved
0.6452	Remote Similarity	NPD3665	Phase 1
0.6422	Remote Similarity	NPD8298	Phase 2
0.6415	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5224	Approved
0.6408	Remote Similarity	NPD4633	Approved
0.6408	Remote Similarity	NPD5211	Phase 2
0.6408	Remote Similarity	NPD5225	Approved
0.6408	Remote Similarity	NPD5226	Approved
0.6381	Remote Similarity	NPD6920	Discontinued
0.6354	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6672	Approved
0.6354	Remote Similarity	NPD5737	Approved
0.6348	Remote Similarity	NPD7604	Phase 2
0.6346	Remote Similarity	NPD5175	Approved
0.6346	Remote Similarity	NPD5174	Approved
0.6346	Remote Similarity	NPD4754	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD7521	Approved
0.63	Remote Similarity	NPD5695	Phase 3
0.6296	Remote Similarity	NPD4634	Approved
0.6286	Remote Similarity	NPD5141	Approved
0.6277	Remote Similarity	NPD3668	Phase 3
0.6275	Remote Similarity	NPD5696	Approved
0.6263	Remote Similarity	NPD8171	Discontinued
0.625	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD7507	Approved
0.6237	Remote Similarity	NPD4223	Phase 3
0.6237	Remote Similarity	NPD4221	Approved
0.6228	Remote Similarity	NPD6319	Approved
0.6226	Remote Similarity	NPD4768	Approved
0.6226	Remote Similarity	NPD6008	Approved
0.6226	Remote Similarity	NPD4767	Approved
0.6211	Remote Similarity	NPD5329	Approved
0.6204	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6001	Approved
0.62	Remote Similarity	NPD7900	Approved
0.6195	Remote Similarity	NPD6335	Approved
0.6186	Remote Similarity	NPD6903	Approved
0.618	Remote Similarity	NPD6942	Approved
0.618	Remote Similarity	NPD7339	Approved
0.6162	Remote Similarity	NPD5284	Approved
0.6162	Remote Similarity	NPD5281	Approved
0.6161	Remote Similarity	NPD6274	Approved
0.6161	Remote Similarity	NPD6868	Approved
0.6154	Remote Similarity	NPD3617	Approved
0.6154	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6098	Approved
0.6146	Remote Similarity	NPD5279	Phase 3
0.614	Remote Similarity	NPD7100	Approved
0.614	Remote Similarity	NPD7101	Approved
0.6139	Remote Similarity	NPD5210	Approved
0.6139	Remote Similarity	NPD4629	Approved
0.6129	Remote Similarity	NPD4139	Approved
0.6129	Remote Similarity	NPD4692	Approved
0.6122	Remote Similarity	NPD6673	Approved
0.6122	Remote Similarity	NPD6904	Approved
0.6122	Remote Similarity	NPD6080	Approved
0.6111	Remote Similarity	NPD4729	Approved
0.6111	Remote Similarity	NPD6933	Approved
0.6111	Remote Similarity	NPD4730	Approved
0.6111	Remote Similarity	NPD5128	Approved
0.6106	Remote Similarity	NPD6317	Approved
0.6105	Remote Similarity	NPD4197	Approved
0.6083	Remote Similarity	NPD7319	Approved
0.6061	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6700	Approved
0.6053	Remote Similarity	NPD6314	Approved
0.6053	Remote Similarity	NPD6313	Approved
0.6047	Remote Similarity	NPD6705	Phase 1
0.6034	Remote Similarity	NPD5983	Phase 2
0.6034	Remote Similarity	NPD6908	Approved
0.6034	Remote Similarity	NPD6909	Approved
0.6026	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD4748	Discontinued
0.6019	Remote Similarity	NPD6412	Phase 2
0.6017	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD5135	Approved
0.6	Remote Similarity	NPD5250	Approved
0.6	Remote Similarity	NPD6703	Approved
0.6	Remote Similarity	NPD3669	Approved
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5248	Approved
0.6	Remote Similarity	NPD5169	Approved
0.6	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5247	Approved
0.6	Remote Similarity	NPD5251	Approved
0.6	Remote Similarity	NPD6702	Approved
0.6	Remote Similarity	NPD5249	Phase 3
0.5979	Remote Similarity	NPD4688	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