NPASS Compound

Structure

NPC472608 OpenBabel07101719142D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.8425 -4.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4316 -3.7831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0186 2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0443 2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3753 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5315 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2191 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -3.4103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 30 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 6 0 0 0 19 26 1 0 0 0 0 19 27 1 1 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 26 1 0 0 0 0 21 31 1 1 0 0 0 22 23 1 0 0 0 0 22 30 1 1 0 0 0 23 25 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 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	517.178
LogP:	4.955
LogD:	4.928
LogS:	-3.766
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	4.811
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:	-5.34
MDCK Permeability:	4.937115954817273e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.9

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	93.57897186279297%
Volume Distribution (VD):	0.79
Pgp-substrate:	2.846548080444336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.395
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.904
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.605
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	2.463
Half-life (T1/2):	0.326

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.722
Carcinogencity:	0.002
Eye Corrosion:	0.497
Eye Irritation:	0.7
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC472608

Natural Product ID:	NPC472608
*Common Name:**	Machaeroceric Acid
IUPAC Name:	(1R,4aR,6aR,6aR,6bR,8aR,10S,12aR,14aR,14bR)-1,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a,14b-hexadecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	WBFQJRAHTVDUSX-TVZSAIOCSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-25(2)14-16-30(24(33)34)17-15-28(6)18(22(30)23(25)32)8-9-20-27(5)12-11-21(31)26(3,4)19(27)10-13-29(20,28)7/h18-23,31-32H,8-17H2,1-7H3,(H,33,34)/t18-,19+,20-,21+,22+,23-,27+,28-,29-,30+/m1/s1
SMILES:	CC1(CCC2(CCC3(C(C2C1O)CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581073
PubChem CID:	24754545
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
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	22690.0	nM	PMID[487526]

☑ 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 NPC472608 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	447
0.1-0.2	3373
0.2-0.3	12394
0.3-0.4	12472
0.4-0.5	5680
0.5-0.6	4616
0.6-0.7	2615
0.7-0.8	981
0.8-0.85	81
0.85-0.9	27
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC243594
0.92	High Similarity	NPC31031
0.92	High Similarity	NPC26029
0.9189	High Similarity	NPC108840
0.9178	High Similarity	NPC168511
0.9178	High Similarity	NPC159325
0.9091	High Similarity	NPC476071
0.9091	High Similarity	NPC280781
0.9091	High Similarity	NPC48756
0.9041	High Similarity	NPC477229
0.9041	High Similarity	NPC68426
0.9041	High Similarity	NPC282905
0.8875	High Similarity	NPC62572
0.8846	High Similarity	NPC474870
0.8846	High Similarity	NPC271572
0.8816	High Similarity	NPC298168
0.8816	High Similarity	NPC143133
0.8816	High Similarity	NPC207010
0.8816	High Similarity	NPC317913
0.88	High Similarity	NPC267753
0.875	High Similarity	NPC473299
0.8684	High Similarity	NPC4209
0.8667	High Similarity	NPC130011
0.859	High Similarity	NPC73013
0.8553	High Similarity	NPC212733
0.8537	High Similarity	NPC187545
0.8519	High Similarity	NPC25037
0.8519	High Similarity	NPC34984
0.85	High Similarity	NPC61107
0.85	High Similarity	NPC30583
0.85	High Similarity	NPC289486
0.8493	Intermediate Similarity	NPC281203
0.8493	Intermediate Similarity	NPC260319
0.8493	Intermediate Similarity	NPC103647
0.8493	Intermediate Similarity	NPC469724
0.8493	Intermediate Similarity	NPC100917
0.8493	Intermediate Similarity	NPC2568
0.8493	Intermediate Similarity	NPC31187
0.8493	Intermediate Similarity	NPC180777
0.8481	Intermediate Similarity	NPC261616
0.8462	Intermediate Similarity	NPC80089
0.8462	Intermediate Similarity	NPC34046
0.8462	Intermediate Similarity	NPC324700
0.8462	Intermediate Similarity	NPC224802
0.8462	Intermediate Similarity	NPC171426
0.8421	Intermediate Similarity	NPC280026
0.8421	Intermediate Similarity	NPC167702
0.84	Intermediate Similarity	NPC247195
0.8375	Intermediate Similarity	NPC50658
0.8354	Intermediate Similarity	NPC320144
0.8354	Intermediate Similarity	NPC201276
0.8354	Intermediate Similarity	NPC80891
0.8353	Intermediate Similarity	NPC472146
0.8353	Intermediate Similarity	NPC290614
0.8353	Intermediate Similarity	NPC227467
0.8353	Intermediate Similarity	NPC50443
0.8353	Intermediate Similarity	NPC18872
0.8353	Intermediate Similarity	NPC18536
0.8353	Intermediate Similarity	NPC210037
0.8353	Intermediate Similarity	NPC273621
0.8353	Intermediate Similarity	NPC477872
0.8353	Intermediate Similarity	NPC185529
0.8353	Intermediate Similarity	NPC120968
0.8353	Intermediate Similarity	NPC7260
0.8333	Intermediate Similarity	NPC112463
0.8333	Intermediate Similarity	NPC23884
0.8312	Intermediate Similarity	NPC174964
0.8312	Intermediate Similarity	NPC97534
0.8312	Intermediate Similarity	NPC195155
0.8293	Intermediate Similarity	NPC219535
0.8293	Intermediate Similarity	NPC237938
0.8289	Intermediate Similarity	NPC475230
0.8289	Intermediate Similarity	NPC81759
0.8272	Intermediate Similarity	NPC121121
0.8256	Intermediate Similarity	NPC187722
0.8256	Intermediate Similarity	NPC105189
0.8235	Intermediate Similarity	NPC64872
0.8235	Intermediate Similarity	NPC67653
0.8235	Intermediate Similarity	NPC471459
0.8235	Intermediate Similarity	NPC25906
0.8235	Intermediate Similarity	NPC290972
0.8228	Intermediate Similarity	NPC185465
0.8205	Intermediate Similarity	NPC5767
0.8205	Intermediate Similarity	NPC475742
0.8193	Intermediate Similarity	NPC131350
0.8161	Intermediate Similarity	NPC118519
0.8161	Intermediate Similarity	NPC229281
0.8161	Intermediate Similarity	NPC158059
0.8161	Intermediate Similarity	NPC472147
0.8161	Intermediate Similarity	NPC202728
0.8161	Intermediate Similarity	NPC472148
0.8158	Intermediate Similarity	NPC89310
0.8158	Intermediate Similarity	NPC290058
0.8148	Intermediate Similarity	NPC12933
0.8148	Intermediate Similarity	NPC58631
0.814	Intermediate Similarity	NPC130278
0.814	Intermediate Similarity	NPC291028
0.814	Intermediate Similarity	NPC193750
0.8118	Intermediate Similarity	NPC182797
0.8118	Intermediate Similarity	NPC474719
0.8118	Intermediate Similarity	NPC3032
0.8118	Intermediate Similarity	NPC473319
0.8118	Intermediate Similarity	NPC131104
0.8118	Intermediate Similarity	NPC52169
0.8108	Intermediate Similarity	NPC41542
0.8101	Intermediate Similarity	NPC221420
0.8101	Intermediate Similarity	NPC307865
0.8095	Intermediate Similarity	NPC120395
0.8095	Intermediate Similarity	NPC83242
0.8095	Intermediate Similarity	NPC72638
0.8095	Intermediate Similarity	NPC248216
0.8095	Intermediate Similarity	NPC2783
0.809	Intermediate Similarity	NPC235109
0.8082	Intermediate Similarity	NPC230047
0.8082	Intermediate Similarity	NPC19311
0.8077	Intermediate Similarity	NPC179858
0.8072	Intermediate Similarity	NPC171789
0.8072	Intermediate Similarity	NPC105895
0.8068	Intermediate Similarity	NPC60692
0.8068	Intermediate Similarity	NPC6818
0.8068	Intermediate Similarity	NPC114159
0.8068	Intermediate Similarity	NPC191412
0.8056	Intermediate Similarity	NPC292419
0.8056	Intermediate Similarity	NPC290791
0.8052	Intermediate Similarity	NPC232112
0.8046	Intermediate Similarity	NPC38754
0.8046	Intermediate Similarity	NPC235704
0.8023	Intermediate Similarity	NPC270768
0.8023	Intermediate Similarity	NPC130520
0.8023	Intermediate Similarity	NPC225585
0.8023	Intermediate Similarity	NPC198664
0.8023	Intermediate Similarity	NPC293048
0.8023	Intermediate Similarity	NPC274330
0.8023	Intermediate Similarity	NPC263393
0.8023	Intermediate Similarity	NPC59263
0.8023	Intermediate Similarity	NPC121798
0.8023	Intermediate Similarity	NPC143232
0.8023	Intermediate Similarity	NPC127689
0.8023	Intermediate Similarity	NPC234346
0.8023	Intermediate Similarity	NPC61543
0.8	Intermediate Similarity	NPC88716
0.8	Intermediate Similarity	NPC242468
0.8	Intermediate Similarity	NPC130577
0.8	Intermediate Similarity	NPC293564
0.8	Intermediate Similarity	NPC171203
0.8	Intermediate Similarity	NPC252714
0.8	Intermediate Similarity	NPC472145
0.8	Intermediate Similarity	NPC329117
0.8	Intermediate Similarity	NPC33768
0.8	Intermediate Similarity	NPC68160
0.8	Intermediate Similarity	NPC475977
0.8	Intermediate Similarity	NPC264005
0.8	Intermediate Similarity	NPC102683
0.8	Intermediate Similarity	NPC18064
0.8	Intermediate Similarity	NPC307426
0.8	Intermediate Similarity	NPC51700
0.8	Intermediate Similarity	NPC98442
0.8	Intermediate Similarity	NPC142415
0.8	Intermediate Similarity	NPC269360
0.7978	Intermediate Similarity	NPC82633
0.7978	Intermediate Similarity	NPC290481
0.7978	Intermediate Similarity	NPC96916
0.7978	Intermediate Similarity	NPC83693
0.7976	Intermediate Similarity	NPC264317
0.7976	Intermediate Similarity	NPC294438
0.7975	Intermediate Similarity	NPC472486
0.7975	Intermediate Similarity	NPC472487
0.7955	Intermediate Similarity	NPC118490
0.7952	Intermediate Similarity	NPC269684
0.7949	Intermediate Similarity	NPC74639
0.7931	Intermediate Similarity	NPC111110
0.7931	Intermediate Similarity	NPC475211
0.7931	Intermediate Similarity	NPC470589
0.7931	Intermediate Similarity	NPC49320
0.7931	Intermediate Similarity	NPC126369
0.7931	Intermediate Similarity	NPC88337
0.7922	Intermediate Similarity	NPC156277
0.7922	Intermediate Similarity	NPC151018
0.7922	Intermediate Similarity	NPC58057
0.7922	Intermediate Similarity	NPC320549
0.7912	Intermediate Similarity	NPC472144
0.7907	Intermediate Similarity	NPC290690
0.7907	Intermediate Similarity	NPC470629
0.7907	Intermediate Similarity	NPC474512
0.7907	Intermediate Similarity	NPC16377
0.7907	Intermediate Similarity	NPC473242
0.7907	Intermediate Similarity	NPC236459
0.7907	Intermediate Similarity	NPC181225
0.7907	Intermediate Similarity	NPC17733
0.7907	Intermediate Similarity	NPC246708
0.7907	Intermediate Similarity	NPC40552
0.7895	Intermediate Similarity	NPC178541
0.7895	Intermediate Similarity	NPC476734
0.7895	Intermediate Similarity	NPC469941
0.7895	Intermediate Similarity	NPC6120
0.7895	Intermediate Similarity	NPC131892
0.7895	Intermediate Similarity	NPC319671
0.7895	Intermediate Similarity	NPC213178
0.7895	Intermediate Similarity	NPC252032
0.7895	Intermediate Similarity	NPC327728

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 NPC472608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	515
0.1-0.2	3574
0.2-0.3	3375
0.3-0.4	1084
0.4-0.5	312
0.5-0.6	225
0.6-0.7	41
0.7-0.8	22
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8816	High Similarity	NPD6116	Phase 1
0.8684	High Similarity	NPD6117	Approved
0.8462	Intermediate Similarity	NPD6115	Approved
0.8462	Intermediate Similarity	NPD6118	Approved
0.8462	Intermediate Similarity	NPD6114	Approved
0.8462	Intermediate Similarity	NPD6697	Approved
0.8421	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD8035	Phase 2
0.7841	Intermediate Similarity	NPD8034	Phase 2
0.7841	Intermediate Similarity	NPD7515	Phase 2
0.7625	Intermediate Similarity	NPD3703	Phase 2
0.7609	Intermediate Similarity	NPD7902	Approved
0.7564	Intermediate Similarity	NPD4245	Approved
0.7564	Intermediate Similarity	NPD4244	Approved
0.75	Intermediate Similarity	NPD4224	Phase 2
0.7473	Intermediate Similarity	NPD7748	Approved
0.7468	Intermediate Similarity	NPD6081	Approved
0.7436	Intermediate Similarity	NPD3698	Phase 2
0.7342	Intermediate Similarity	NPD4789	Approved
0.7308	Intermediate Similarity	NPD5360	Phase 3
0.7308	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7900	Approved
0.7283	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5777	Approved
0.7143	Intermediate Similarity	NPD3671	Phase 1
0.7143	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3702	Approved
0.6944	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4758	Discontinued
0.6809	Remote Similarity	NPD6399	Phase 3
0.6744	Remote Similarity	NPD5364	Discontinued
0.6735	Remote Similarity	NPD8418	Phase 2
0.6703	Remote Similarity	NPD3618	Phase 1
0.6699	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7645	Phase 2
0.6574	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4787	Phase 1
0.6494	Remote Similarity	NPD3198	Approved
0.6489	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5328	Approved
0.6486	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4786	Approved
0.6471	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7638	Approved
0.6444	Remote Similarity	NPD3667	Approved
0.6442	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6402	Approved
0.6408	Remote Similarity	NPD7128	Approved
0.6408	Remote Similarity	NPD5739	Approved
0.6408	Remote Similarity	NPD6675	Approved
0.6404	Remote Similarity	NPD7525	Registered
0.6404	Remote Similarity	NPD6928	Phase 2
0.64	Remote Similarity	NPD7640	Approved
0.64	Remote Similarity	NPD7639	Approved
0.6381	Remote Similarity	NPD6372	Approved
0.6381	Remote Similarity	NPD6373	Approved
0.6375	Remote Similarity	NPD7909	Approved
0.6374	Remote Similarity	NPD4788	Approved
0.6354	Remote Similarity	NPD6079	Approved
0.6296	Remote Similarity	NPD8133	Approved
0.6289	Remote Similarity	NPD4202	Approved
0.6286	Remote Similarity	NPD6881	Approved
0.6286	Remote Similarity	NPD7320	Approved
0.6286	Remote Similarity	NPD6899	Approved
0.6275	Remote Similarity	NPD7632	Discontinued
0.6263	Remote Similarity	NPD4697	Phase 3
0.6262	Remote Similarity	NPD6650	Approved
0.6262	Remote Similarity	NPD6649	Approved
0.6228	Remote Similarity	NPD8328	Phase 3
0.6211	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4755	Approved
0.6196	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD3669	Approved
0.619	Remote Similarity	NPD5697	Approved
0.619	Remote Similarity	NPD5701	Approved
0.6168	Remote Similarity	NPD6883	Approved
0.6168	Remote Similarity	NPD7290	Approved
0.6168	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD1780	Approved
0.6154	Remote Similarity	NPD1779	Approved
0.6132	Remote Similarity	NPD6011	Approved
0.6129	Remote Similarity	NPD3665	Phase 1
0.6129	Remote Similarity	NPD3133	Approved
0.6129	Remote Similarity	NPD3666	Approved
0.6111	Remote Similarity	NPD6847	Approved
0.6111	Remote Similarity	NPD6869	Approved
0.6111	Remote Similarity	NPD6617	Approved
0.6111	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8130	Phase 1
0.61	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5222	Approved
0.61	Remote Similarity	NPD5221	Approved
0.61	Remote Similarity	NPD7614	Phase 1
0.6078	Remote Similarity	NPD5285	Approved
0.6078	Remote Similarity	NPD5286	Approved
0.6078	Remote Similarity	NPD4696	Approved
0.6078	Remote Similarity	NPD4700	Approved
0.6075	Remote Similarity	NPD6013	Approved
0.6075	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6014	Approved
0.6075	Remote Similarity	NPD6012	Approved
0.6071	Remote Similarity	NPD229	Approved
0.6055	Remote Similarity	NPD6882	Approved
0.6055	Remote Similarity	NPD8297	Approved
0.604	Remote Similarity	NPD6084	Phase 2
0.604	Remote Similarity	NPD5173	Approved
0.604	Remote Similarity	NPD6083	Phase 2
0.6036	Remote Similarity	NPD6940	Discontinued
0.602	Remote Similarity	NPD6411	Approved
0.6019	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.6	Remote Similarity	NPD8298	Phase 2
0.5982	Remote Similarity	NPD7115	Discovery
0.5972	Remote Similarity	NPD384	Approved
0.5972	Remote Similarity	NPD385	Approved
0.5962	Remote Similarity	NPD5225	Approved
0.5962	Remote Similarity	NPD4633	Approved
0.5962	Remote Similarity	NPD5226	Approved
0.5962	Remote Similarity	NPD5224	Approved
0.5962	Remote Similarity	NPD5211	Phase 2
0.596	Remote Similarity	NPD8171	Discontinued
0.5957	Remote Similarity	NPD3668	Phase 3
0.5943	Remote Similarity	NPD6920	Discontinued
0.5938	Remote Similarity	NPD3573	Approved
0.5905	Remote Similarity	NPD5174	Approved
0.5905	Remote Similarity	NPD4754	Approved
0.5905	Remote Similarity	NPD5175	Approved
0.5876	Remote Similarity	NPD6672	Approved
0.5876	Remote Similarity	NPD5737	Approved
0.5876	Remote Similarity	NPD6903	Approved
0.5865	Remote Similarity	NPD1700	Approved
0.5859	Remote Similarity	NPD5281	Approved
0.5859	Remote Similarity	NPD5284	Approved
0.5856	Remote Similarity	NPD4632	Approved
0.5849	Remote Similarity	NPD5141	Approved
0.5842	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD634	Phase 3
0.5825	Remote Similarity	NPD5696	Approved
0.5825	Remote Similarity	NPD4225	Approved
0.5824	Remote Similarity	NPD3617	Approved
0.5824	Remote Similarity	NPD4802	Phase 2
0.5824	Remote Similarity	NPD4238	Approved
0.5816	Remote Similarity	NPD4753	Phase 2
0.5816	Remote Similarity	NPD6101	Approved
0.5816	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD3726	Approved
0.5814	Remote Similarity	NPD3725	Approved
0.5794	Remote Similarity	NPD6008	Approved
0.5794	Remote Similarity	NPD4768	Approved
0.5794	Remote Similarity	NPD4767	Approved
0.5789	Remote Similarity	NPD3186	Phase 1
0.5789	Remote Similarity	NPD6335	Approved
0.5784	Remote Similarity	NPD7732	Phase 3
0.5776	Remote Similarity	NPD6921	Approved
0.5752	Remote Similarity	NPD6868	Approved
0.5752	Remote Similarity	NPD6274	Approved
0.5741	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6412	Phase 2
0.5741	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD7100	Approved
0.5739	Remote Similarity	NPD7101	Approved
0.5714	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7507	Approved
0.5702	Remote Similarity	NPD6009	Approved
0.5702	Remote Similarity	NPD6317	Approved
0.5699	Remote Similarity	NPD4695	Discontinued
0.5688	Remote Similarity	NPD5128	Approved
0.5688	Remote Similarity	NPD6415	Discontinued
0.5688	Remote Similarity	NPD4730	Approved
0.5688	Remote Similarity	NPD6686	Approved
0.5688	Remote Similarity	NPD4729	Approved
0.5686	Remote Similarity	NPD5210	Approved
0.5686	Remote Similarity	NPD5695	Phase 3
0.5686	Remote Similarity	NPD4629	Approved
0.5676	Remote Similarity	NPD2266	Phase 2
0.567	Remote Similarity	NPD5279	Phase 3
0.5667	Remote Similarity	NPD6942	Approved
0.5667	Remote Similarity	NPD7339	Approved
0.5652	Remote Similarity	NPD6314	Approved
0.5652	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6313	Approved
0.5641	Remote Similarity	NPD3730	Approved
0.5641	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD3728	Approved
0.5641	Remote Similarity	NPD6908	Approved
0.5641	Remote Similarity	NPD6909	Approved
0.562	Remote Similarity	NPD7736	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