NPASS Compound

Structure

NPC474174 OpenBabel07101719512D 34 37 0 0 1 0 0 0 0 0999 V2000 3.3373 4.1600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4895 -1.5123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9895 -2.3784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0786 -2.4719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4370 -1.5384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4950 1.5922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2216 0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5395 1.0046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0502 3.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6920 2.5703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0987 1.6568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7412 2.0500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6235 -0.0123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2216 -1.5123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5981 -0.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6235 0.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2216 -0.5123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 0.7346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0283 3.2089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6975 2.4658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4895 -0.5123 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3556 0.9877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3556 -2.0123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7630 1.8421 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4895 -1.5123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5507 -1.6948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4895 1.4877 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3556 -0.0123 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4540 0.8910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3556 -3.0123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0939 2.5852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3278 -2.3241 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 1 19 2 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 20 28 1 1 0 0 0 21 26 1 0 0 0 0 21 29 1 6 0 0 0 22 28 1 6 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 31 2 0 0 0 0 24 30 1 0 0 0 0 24 32 1 6 0 0 0 25 27 1 6 0 0 0 25 34 1 0 0 0 0 27 33 1 0 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 1 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	523.098
LogP:	4.856
LogD:	4.29
LogS:	-4.384
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	5.041
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.949
MDCK Permeability:	1.2372943274385761e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.203
30% Bioavailability (F30%):	0.824

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	87.60340881347656%
Volume Distribution (VD):	1.038
Pgp-substrate:	4.285595417022705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.285
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.159
CYP2C9-substrate:	0.36
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.701
CYP3A4-inhibitor:	0.303
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	6.54
Half-life (T1/2):	0.275

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.42
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.145
Maximum Recommended Daily Dose:	0.797
Skin Sensitization:	0.243
Carcinogencity:	0.038
Eye Corrosion:	0.006
Eye Irritation:	0.04
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC474174

Natural Product ID:	NPC474174
*Common Name:**	(17R,20S,24R)-17,25-Dihydroxy-20,24-Epoxy-14(18)-Malabaricen-3-One
IUPAC Name:	(3R,3aS,5aR,9aR,9bS)-3-[(5R)-5-hydroxy-5-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]pent-1-en-2-yl]-3a,6,6,9a-tetramethyl-2,3,4,5,5a,8,9,9b-octahydro-1H-cyclopenta[a]naphthalen-7-one
Synonyms:
Standard InCHIKey:	SBYBESQWVAOXTK-ZLBCXZKWSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-19(9-12-24(32)30(8)18-15-25(34-30)27(4,5)33)20-10-11-22-28(20,6)16-13-21-26(2,3)23(31)14-17-29(21,22)7/h20-22,24-25,32-33H,1,9-18H2,2-8H3/t20-,21+,22+,24-,25-,28+,29+,30+/m1/s1
SMILES:	CC1(C2CCC3(C(CCC3C2(CCC1=O)C)C(=C)CCC(C4(CCC(O4)C(C)(C)O)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463240
PubChem CID:	10994383
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO22998	Caloncoba echinata	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502310]
NPO22998	Caloncoba echinata	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	<	12.0	ug.mL-1	PMID[493518]

☑ 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 NPC474174 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	185
0.1-0.2	1402
0.2-0.3	6221
0.3-0.4	15483
0.4-0.5	6141
0.5-0.6	5877
0.6-0.7	6208
0.7-0.8	1117
0.8-0.85	48
0.85-0.9	7
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC251808
0.9405	High Similarity	NPC254572
0.9405	High Similarity	NPC229407
0.9405	High Similarity	NPC48824
0.9405	High Similarity	NPC250687
0.9302	High Similarity	NPC471747
0.9294	High Similarity	NPC269267
0.8736	High Similarity	NPC255176
0.8588	High Similarity	NPC268578
0.8588	High Similarity	NPC292458
0.8588	High Similarity	NPC217559
0.8554	High Similarity	NPC245029
0.8554	High Similarity	NPC31302
0.8471	Intermediate Similarity	NPC311642
0.8471	Intermediate Similarity	NPC242771
0.8471	Intermediate Similarity	NPC164289
0.8471	Intermediate Similarity	NPC100366
0.8462	Intermediate Similarity	NPC174051
0.8462	Intermediate Similarity	NPC67831
0.8444	Intermediate Similarity	NPC262870
0.8438	Intermediate Similarity	NPC121566
0.8438	Intermediate Similarity	NPC100955
0.8409	Intermediate Similarity	NPC90652
0.8404	Intermediate Similarity	NPC167974
0.8353	Intermediate Similarity	NPC232625
0.8351	Intermediate Similarity	NPC63023
0.8351	Intermediate Similarity	NPC95243
0.8315	Intermediate Similarity	NPC470417
0.8295	Intermediate Similarity	NPC475007
0.8295	Intermediate Similarity	NPC80700
0.8295	Intermediate Similarity	NPC474448
0.8256	Intermediate Similarity	NPC102156
0.8256	Intermediate Similarity	NPC145143
0.8256	Intermediate Similarity	NPC148740
0.8247	Intermediate Similarity	NPC471293
0.8247	Intermediate Similarity	NPC255309
0.8235	Intermediate Similarity	NPC164999
0.8235	Intermediate Similarity	NPC170038
0.8222	Intermediate Similarity	NPC32830
0.8191	Intermediate Similarity	NPC253586
0.8163	Intermediate Similarity	NPC96377
0.8132	Intermediate Similarity	NPC46758
0.8118	Intermediate Similarity	NPC118987
0.8118	Intermediate Similarity	NPC201459
0.8111	Intermediate Similarity	NPC193360
0.809	Intermediate Similarity	NPC473168
0.8046	Intermediate Similarity	NPC477858
0.8021	Intermediate Similarity	NPC108371
0.8	Intermediate Similarity	NPC469322
0.8	Intermediate Similarity	NPC170978
0.8	Intermediate Similarity	NPC258323
0.8	Intermediate Similarity	NPC167877
0.8	Intermediate Similarity	NPC190080
0.8	Intermediate Similarity	NPC224414
0.8	Intermediate Similarity	NPC111187
0.7979	Intermediate Similarity	NPC279974
0.7959	Intermediate Similarity	NPC471005
0.7957	Intermediate Similarity	NPC291373
0.7955	Intermediate Similarity	NPC472743
0.7955	Intermediate Similarity	NPC471037
0.7955	Intermediate Similarity	NPC86370
0.7955	Intermediate Similarity	NPC475726
0.7938	Intermediate Similarity	NPC476897
0.7935	Intermediate Similarity	NPC136801
0.7935	Intermediate Similarity	NPC171441
0.7935	Intermediate Similarity	NPC289213
0.7931	Intermediate Similarity	NPC474484
0.7931	Intermediate Similarity	NPC103754
0.7912	Intermediate Similarity	NPC44181
0.7912	Intermediate Similarity	NPC473436
0.7907	Intermediate Similarity	NPC476812
0.79	Intermediate Similarity	NPC59530
0.7889	Intermediate Similarity	NPC70661
0.7889	Intermediate Similarity	NPC80590
0.7889	Intermediate Similarity	NPC89077
0.7889	Intermediate Similarity	NPC472745
0.7889	Intermediate Similarity	NPC92139
0.7882	Intermediate Similarity	NPC149249
0.7882	Intermediate Similarity	NPC106078
0.7872	Intermediate Similarity	NPC277399
0.7872	Intermediate Similarity	NPC318332
0.7872	Intermediate Similarity	NPC47853
0.7865	Intermediate Similarity	NPC474482
0.7865	Intermediate Similarity	NPC474233
0.7865	Intermediate Similarity	NPC85774
0.7865	Intermediate Similarity	NPC475745
0.7865	Intermediate Similarity	NPC59453
0.7865	Intermediate Similarity	NPC82902
0.7865	Intermediate Similarity	NPC214043
0.7865	Intermediate Similarity	NPC221758
0.7864	Intermediate Similarity	NPC207251
0.7857	Intermediate Similarity	NPC473928
0.7857	Intermediate Similarity	NPC94919
0.7849	Intermediate Similarity	NPC473166
0.7843	Intermediate Similarity	NPC101450
0.7843	Intermediate Similarity	NPC106760
0.7835	Intermediate Similarity	NPC83709
0.7826	Intermediate Similarity	NPC253618
0.7826	Intermediate Similarity	NPC186688
0.7826	Intermediate Similarity	NPC215029
0.7826	Intermediate Similarity	NPC474245
0.7826	Intermediate Similarity	NPC77001
0.7826	Intermediate Similarity	NPC220498
0.7826	Intermediate Similarity	NPC476733
0.7822	Intermediate Similarity	NPC255082
0.7812	Intermediate Similarity	NPC27105
0.7812	Intermediate Similarity	NPC272451
0.7812	Intermediate Similarity	NPC475894
0.7802	Intermediate Similarity	NPC33768
0.7802	Intermediate Similarity	NPC259009
0.7802	Intermediate Similarity	NPC99909
0.7802	Intermediate Similarity	NPC134197
0.7802	Intermediate Similarity	NPC138756
0.7802	Intermediate Similarity	NPC153604
0.7802	Intermediate Similarity	NPC317590
0.78	Intermediate Similarity	NPC472655
0.7789	Intermediate Similarity	NPC98639
0.7788	Intermediate Similarity	NPC178981
0.7778	Intermediate Similarity	NPC471224
0.7778	Intermediate Similarity	NPC140723
0.7778	Intermediate Similarity	NPC471034
0.7778	Intermediate Similarity	NPC277074
0.7778	Intermediate Similarity	NPC474218
0.7778	Intermediate Similarity	NPC76518
0.7778	Intermediate Similarity	NPC190704
0.7778	Intermediate Similarity	NPC201655
0.7778	Intermediate Similarity	NPC292553
0.7778	Intermediate Similarity	NPC221421
0.7778	Intermediate Similarity	NPC209298
0.7767	Intermediate Similarity	NPC272242
0.7766	Intermediate Similarity	NPC224060
0.7766	Intermediate Similarity	NPC98193
0.7766	Intermediate Similarity	NPC198074
0.7766	Intermediate Similarity	NPC274046
0.7766	Intermediate Similarity	NPC470224
0.7766	Intermediate Similarity	NPC244356
0.7765	Intermediate Similarity	NPC476601
0.7755	Intermediate Similarity	NPC252614
0.7753	Intermediate Similarity	NPC245866
0.7753	Intermediate Similarity	NPC175410
0.7753	Intermediate Similarity	NPC472744
0.7745	Intermediate Similarity	NPC8431
0.7745	Intermediate Similarity	NPC170221
0.7745	Intermediate Similarity	NPC10064
0.7742	Intermediate Similarity	NPC320026
0.7732	Intermediate Similarity	NPC203388
0.7732	Intermediate Similarity	NPC472687
0.7732	Intermediate Similarity	NPC99657
0.7732	Intermediate Similarity	NPC471330
0.7732	Intermediate Similarity	NPC471331
0.7732	Intermediate Similarity	NPC119036
0.7723	Intermediate Similarity	NPC131665
0.7723	Intermediate Similarity	NPC255387
0.7717	Intermediate Similarity	NPC211162
0.7717	Intermediate Similarity	NPC4309
0.7717	Intermediate Similarity	NPC474719
0.7717	Intermediate Similarity	NPC183374
0.7714	Intermediate Similarity	NPC326542
0.7708	Intermediate Similarity	NPC260223
0.7708	Intermediate Similarity	NPC329910
0.7708	Intermediate Similarity	NPC49371
0.7708	Intermediate Similarity	NPC200054
0.7708	Intermediate Similarity	NPC29410
0.7708	Intermediate Similarity	NPC256227
0.7701	Intermediate Similarity	NPC215843
0.77	Intermediate Similarity	NPC75531
0.77	Intermediate Similarity	NPC149124
0.77	Intermediate Similarity	NPC301787
0.7692	Intermediate Similarity	NPC470051
0.7692	Intermediate Similarity	NPC12774
0.7692	Intermediate Similarity	NPC474733
0.7692	Intermediate Similarity	NPC472505
0.7692	Intermediate Similarity	NPC51014
0.7692	Intermediate Similarity	NPC469994
0.7692	Intermediate Similarity	NPC472738
0.7692	Intermediate Similarity	NPC474732
0.7692	Intermediate Similarity	NPC2783
0.7692	Intermediate Similarity	NPC145879
0.7692	Intermediate Similarity	NPC31564
0.7692	Intermediate Similarity	NPC470050
0.7692	Intermediate Similarity	NPC474778
0.7684	Intermediate Similarity	NPC111015
0.7684	Intermediate Similarity	NPC196485
0.7684	Intermediate Similarity	NPC245972
0.7677	Intermediate Similarity	NPC124544
0.7674	Intermediate Similarity	NPC325946
0.7674	Intermediate Similarity	NPC66105
0.7674	Intermediate Similarity	NPC264602
0.767	Intermediate Similarity	NPC475563
0.767	Intermediate Similarity	NPC470065
0.767	Intermediate Similarity	NPC52241
0.767	Intermediate Similarity	NPC475134
0.767	Intermediate Similarity	NPC5284
0.767	Intermediate Similarity	NPC154856
0.767	Intermediate Similarity	NPC6206
0.767	Intermediate Similarity	NPC475317
0.7667	Intermediate Similarity	NPC74595
0.7667	Intermediate Similarity	NPC100391
0.7667	Intermediate Similarity	NPC473157
0.7667	Intermediate Similarity	NPC263974

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 NPC474174 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1973
0.2-0.3	4240
0.3-0.4	1898
0.4-0.5	413
0.5-0.6	190
0.6-0.7	212
0.7-0.8	63
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
0.7955	Intermediate Similarity	NPD4788	Approved
0.7865	Intermediate Similarity	NPD4786	Approved
0.764	Intermediate Similarity	NPD3667	Approved
0.7582	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6399	Phase 3
0.7549	Intermediate Similarity	NPD6412	Phase 2
0.7474	Intermediate Similarity	NPD8035	Phase 2
0.7474	Intermediate Similarity	NPD8034	Phase 2
0.7473	Intermediate Similarity	NPD3666	Approved
0.7473	Intermediate Similarity	NPD3665	Phase 1
0.7473	Intermediate Similarity	NPD3133	Approved
0.7449	Intermediate Similarity	NPD6084	Phase 2
0.7449	Intermediate Similarity	NPD6083	Phase 2
0.7447	Intermediate Similarity	NPD5328	Approved
0.7447	Intermediate Similarity	NPD4753	Phase 2
0.7419	Intermediate Similarity	NPD7524	Approved
0.7407	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3618	Phase 1
0.7294	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6079	Approved
0.7253	Intermediate Similarity	NPD4223	Phase 3
0.7253	Intermediate Similarity	NPD4221	Approved
0.7216	Intermediate Similarity	NPD4202	Approved
0.7207	Intermediate Similarity	NPD6059	Approved
0.7207	Intermediate Similarity	NPD6054	Approved
0.7204	Intermediate Similarity	NPD5329	Approved
0.7191	Intermediate Similarity	NPD6115	Approved
0.7191	Intermediate Similarity	NPD6118	Approved
0.7191	Intermediate Similarity	NPD6114	Approved
0.7191	Intermediate Similarity	NPD6697	Approved
0.7176	Intermediate Similarity	NPD4245	Approved
0.7176	Intermediate Similarity	NPD4244	Approved
0.7176	Intermediate Similarity	NPD4789	Approved
0.7174	Intermediate Similarity	NPD6695	Phase 3
0.7159	Intermediate Similarity	NPD6933	Approved
0.7158	Intermediate Similarity	NPD6903	Approved
0.7158	Intermediate Similarity	NPD5737	Approved
0.7158	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD7320	Approved
0.713	Intermediate Similarity	NPD8133	Approved
0.713	Intermediate Similarity	NPD4632	Approved
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7128	Intermediate Similarity	NPD7521	Approved
0.7128	Intermediate Similarity	NPD7334	Approved
0.7128	Intermediate Similarity	NPD6684	Approved
0.7128	Intermediate Similarity	NPD7146	Approved
0.7128	Intermediate Similarity	NPD6409	Approved
0.7128	Intermediate Similarity	NPD5330	Approved
0.7115	Intermediate Similarity	NPD5739	Approved
0.7115	Intermediate Similarity	NPD6675	Approved
0.7115	Intermediate Similarity	NPD6402	Approved
0.7115	Intermediate Similarity	NPD7128	Approved
0.71	Intermediate Similarity	NPD4755	Approved
0.7097	Intermediate Similarity	NPD3668	Phase 3
0.7097	Intermediate Similarity	NPD4197	Approved
0.7097	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6370	Approved
0.7071	Intermediate Similarity	NPD4629	Approved
0.7071	Intermediate Similarity	NPD5695	Phase 3
0.7071	Intermediate Similarity	NPD5210	Approved
0.7071	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3698	Phase 2
0.7059	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3703	Phase 2
0.7037	Intermediate Similarity	NPD8297	Approved
0.7033	Intermediate Similarity	NPD7525	Registered
0.703	Intermediate Similarity	NPD5696	Approved
0.703	Intermediate Similarity	NPD7638	Approved
0.7009	Intermediate Similarity	NPD4634	Approved
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD4697	Phase 3
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6015	Approved
0.6991	Remote Similarity	NPD6016	Approved
0.6981	Remote Similarity	NPD6899	Approved
0.6981	Remote Similarity	NPD6881	Approved
0.6979	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6117	Approved
0.6961	Remote Similarity	NPD7639	Approved
0.6961	Remote Similarity	NPD5286	Approved
0.6961	Remote Similarity	NPD5285	Approved
0.6961	Remote Similarity	NPD4700	Approved
0.6961	Remote Similarity	NPD4696	Approved
0.6961	Remote Similarity	NPD7640	Approved
0.6957	Remote Similarity	NPD7492	Approved
0.6952	Remote Similarity	NPD6008	Approved
0.6947	Remote Similarity	NPD4693	Phase 3
0.6947	Remote Similarity	NPD4138	Approved
0.6947	Remote Similarity	NPD4689	Approved
0.6947	Remote Similarity	NPD4690	Approved
0.6947	Remote Similarity	NPD5205	Approved
0.6947	Remote Similarity	NPD4688	Approved
0.6947	Remote Similarity	NPD6098	Approved
0.6941	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5360	Phase 3
0.6937	Remote Similarity	NPD7115	Discovery
0.6932	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6926	Approved
0.6932	Remote Similarity	NPD6924	Approved
0.6931	Remote Similarity	NPD5173	Approved
0.693	Remote Similarity	NPD5988	Approved
0.6916	Remote Similarity	NPD6373	Approved
0.6916	Remote Similarity	NPD6372	Approved
0.6907	Remote Similarity	NPD6673	Approved
0.6907	Remote Similarity	NPD6904	Approved
0.6907	Remote Similarity	NPD6080	Approved
0.6903	Remote Similarity	NPD6319	Approved
0.6897	Remote Similarity	NPD6616	Approved
0.6893	Remote Similarity	NPD5223	Approved
0.6889	Remote Similarity	NPD6116	Phase 1
0.6887	Remote Similarity	NPD5697	Approved
0.6887	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD7750	Discontinued
0.6857	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3702	Approved
0.6854	Remote Similarity	NPD7339	Approved
0.6854	Remote Similarity	NPD6942	Approved
0.6852	Remote Similarity	NPD6883	Approved
0.6852	Remote Similarity	NPD7290	Approved
0.6852	Remote Similarity	NPD7102	Approved
0.6848	Remote Similarity	NPD6930	Phase 2
0.6848	Remote Similarity	NPD6931	Approved
0.6838	Remote Similarity	NPD7078	Approved
0.6838	Remote Similarity	NPD8293	Discontinued
0.6827	Remote Similarity	NPD5211	Phase 2
0.6827	Remote Similarity	NPD5225	Approved
0.6827	Remote Similarity	NPD5224	Approved
0.6827	Remote Similarity	NPD4633	Approved
0.6827	Remote Similarity	NPD5226	Approved
0.6822	Remote Similarity	NPD6011	Approved
0.6822	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6686	Approved
0.6813	Remote Similarity	NPD3617	Approved
0.68	Remote Similarity	NPD7748	Approved
0.6789	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8130	Phase 1
0.6789	Remote Similarity	NPD6847	Approved
0.6789	Remote Similarity	NPD6650	Approved
0.6789	Remote Similarity	NPD6869	Approved
0.6789	Remote Similarity	NPD6617	Approved
0.6789	Remote Similarity	NPD6649	Approved
0.6786	Remote Similarity	NPD6009	Approved
0.678	Remote Similarity	NPD6033	Approved
0.678	Remote Similarity	NPD7736	Approved
0.6774	Remote Similarity	NPD4139	Approved
0.6774	Remote Similarity	NPD4692	Approved
0.6771	Remote Similarity	NPD5690	Phase 2
0.6771	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5280	Approved
0.6771	Remote Similarity	NPD4694	Approved
0.6768	Remote Similarity	NPD7515	Phase 2
0.6768	Remote Similarity	NPD7637	Suspended
0.6762	Remote Similarity	NPD5174	Approved
0.6762	Remote Similarity	NPD4754	Approved
0.6762	Remote Similarity	NPD5175	Approved
0.6759	Remote Similarity	NPD6014	Approved
0.6759	Remote Similarity	NPD6012	Approved
0.6759	Remote Similarity	NPD6013	Approved
0.6752	Remote Similarity	NPD7507	Approved
0.6739	Remote Similarity	NPD6929	Approved
0.6727	Remote Similarity	NPD6882	Approved
0.6724	Remote Similarity	NPD7604	Phase 2
0.6724	Remote Similarity	NPD6067	Discontinued
0.6705	Remote Similarity	NPD6081	Approved
0.6705	Remote Similarity	NPD5777	Approved
0.6703	Remote Similarity	NPD6932	Approved
0.6698	Remote Similarity	NPD5141	Approved
0.6696	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5207	Approved
0.6636	Remote Similarity	NPD4768	Approved
0.6636	Remote Similarity	NPD4767	Approved
0.6634	Remote Similarity	NPD6001	Approved
0.6634	Remote Similarity	NPD5282	Discontinued
0.6633	Remote Similarity	NPD5208	Approved
0.663	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6336	Discontinued
0.6606	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7902	Approved
0.66	Remote Similarity	NPD5693	Phase 1
0.66	Remote Similarity	NPD7087	Discontinued
0.66	Remote Similarity	NPD5281	Approved
0.66	Remote Similarity	NPD5284	Approved
0.66	Remote Similarity	NPD6050	Approved
0.6593	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7319	Approved
0.6559	Remote Similarity	NPD4195	Approved
0.6559	Remote Similarity	NPD6683	Phase 2
0.6538	Remote Similarity	NPD4225	Approved
0.6531	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5956	Approved
0.6522	Remote Similarity	NPD4522	Approved
0.6522	Remote Similarity	NPD6925	Approved
0.6522	Remote Similarity	NPD5776	Phase 2
0.6517	Remote Similarity	NPD4243	Approved
0.6517	Remote Similarity	NPD4758	Discontinued

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