NPASS Compound

Structure

CID31031 OpenBabel06191715362D 36 40 0 0 1 0 0 0 0 0999 V2000 2.5347 -4.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2001 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7123 -0.3571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5103 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 -0.6185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 -2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 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 -2.5347 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2245 -4.3902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 29 1 0 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 30 1 0 0 0 0 17 32 1 0 0 0 0 18 32 1 0 0 0 0 19 22 1 0 0 0 0 19 27 1 0 0 0 0 20 33 2 0 0 0 0 20 36 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 6 0 0 0 22 32 1 6 0 0 0 23 28 1 0 0 0 0 23 29 1 1 0 0 0 24 29 1 1 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 36 1 1 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 8 1 1 0 0 0 32 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.39
Volume:	549.134
LogP:	6.855
LogD:	5.748
LogS:	-5.438
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.392
Synthetic Accessibility Score:	4.676
Fsp3:	0.938
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.24
MDCK Permeability:	2.72412125923438e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.119
30% Bioavailability (F30%):	0.872

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	90.4967269897461%
Volume Distribution (VD):	0.853
Pgp-substrate:	2.045494794845581%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.145
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.57
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	2.221
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.544
Skin Sensitization:	0.55
Carcinogencity:	0.014
Eye Corrosion:	0.954
Eye Irritation:	0.709
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC31031

Natural Product ID:	NPC31031
*Common Name:**	Oleananoic Acid Acetate
IUPAC Name:	(4aS,6aR,6aR,6bR,8aR,10S,12aR,14aR,14bS)-10-acetyloxy-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:	YDHTWQABZAECEX-ABUCSYTDSA-N
Standard InCHI:	InChI=1S/C32H52O4/c1-20(33)36-25-12-13-29(6)23(28(25,4)5)11-14-31(8)24(29)10-9-21-22-19-27(2,3)15-17-32(22,26(34)35)18-16-30(21,31)7/h21-25H,9-19H2,1-8H3,(H,34,35)/t21-,22+,23+,24-,25+,29+,30-,31-,32+/m1/s1
SMILES:	CC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC[C@@H]2[C@@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3138657
PubChem CID:	76336789
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
NPO28722	Radermachera xylocarpa	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24317	Primula integrifolia	Species	Primulaceae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	112.29	%	PMID[454374]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	103.73	%	PMID[454374]

☑ 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 NPC31031 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	444
0.1-0.2	3270
0.2-0.3	11893
0.3-0.4	12978
0.4-0.5	5703
0.5-0.6	4702
0.6-0.7	2626
0.7-0.8	980
0.8-0.85	67
0.85-0.9	29
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC243594
0.9211	High Similarity	NPC261616
0.92	High Similarity	NPC472608
0.9091	High Similarity	NPC280781
0.9091	High Similarity	NPC271572
0.9091	High Similarity	NPC474870
0.9091	High Similarity	NPC48756
0.9079	High Similarity	NPC73013
0.8947	High Similarity	NPC26029
0.8875	High Similarity	NPC62572
0.8846	High Similarity	NPC476071
0.8784	High Similarity	NPC477229
0.8784	High Similarity	NPC68426
0.8784	High Similarity	NPC475230
0.8784	High Similarity	NPC282905
0.8734	High Similarity	NPC289486
0.8734	High Similarity	NPC61107
0.8684	High Similarity	NPC108840
0.8667	High Similarity	NPC159325
0.8667	High Similarity	NPC74639
0.8667	High Similarity	NPC168511
0.8571	High Similarity	NPC143133
0.8571	High Similarity	NPC298168
0.8553	High Similarity	NPC267753
0.8519	High Similarity	NPC473299
0.8519	High Similarity	NPC219535
0.8519	High Similarity	NPC237938
0.8493	Intermediate Similarity	NPC281203
0.8493	Intermediate Similarity	NPC469724
0.8493	Intermediate Similarity	NPC100917
0.8493	Intermediate Similarity	NPC31187
0.8452	Intermediate Similarity	NPC30522
0.8442	Intermediate Similarity	NPC4209
0.8421	Intermediate Similarity	NPC130011
0.8378	Intermediate Similarity	NPC178541
0.8375	Intermediate Similarity	NPC50658
0.8356	Intermediate Similarity	NPC41542
0.8354	Intermediate Similarity	NPC201276
0.8354	Intermediate Similarity	NPC80891
0.8353	Intermediate Similarity	NPC113989
0.8353	Intermediate Similarity	NPC185529
0.8353	Intermediate Similarity	NPC472146
0.8353	Intermediate Similarity	NPC120840
0.8353	Intermediate Similarity	NPC18536
0.8353	Intermediate Similarity	NPC50443
0.8333	Intermediate Similarity	NPC207010
0.8333	Intermediate Similarity	NPC112463
0.8333	Intermediate Similarity	NPC317913
0.8333	Intermediate Similarity	NPC4309
0.8313	Intermediate Similarity	NPC83242
0.8313	Intermediate Similarity	NPC187545
0.8312	Intermediate Similarity	NPC212733
0.8293	Intermediate Similarity	NPC34984
0.8293	Intermediate Similarity	NPC25037
0.8293	Intermediate Similarity	NPC319909
0.8293	Intermediate Similarity	NPC105895
0.8272	Intermediate Similarity	NPC30583
0.8256	Intermediate Similarity	NPC285184
0.8256	Intermediate Similarity	NPC470590
0.8256	Intermediate Similarity	NPC77099
0.8256	Intermediate Similarity	NPC60755
0.8243	Intermediate Similarity	NPC2568
0.8243	Intermediate Similarity	NPC180777
0.8243	Intermediate Similarity	NPC103647
0.8243	Intermediate Similarity	NPC260319
0.8228	Intermediate Similarity	NPC80089
0.8228	Intermediate Similarity	NPC34046
0.8228	Intermediate Similarity	NPC171426
0.8228	Intermediate Similarity	NPC324700
0.8228	Intermediate Similarity	NPC224802
0.8214	Intermediate Similarity	NPC252714
0.8182	Intermediate Similarity	NPC167702
0.8182	Intermediate Similarity	NPC280026
0.8171	Intermediate Similarity	NPC269684
0.8161	Intermediate Similarity	NPC86368
0.8161	Intermediate Similarity	NPC472147
0.8161	Intermediate Similarity	NPC472148
0.8158	Intermediate Similarity	NPC247195
0.8158	Intermediate Similarity	NPC469940
0.8148	Intermediate Similarity	NPC58631
0.814	Intermediate Similarity	NPC88337
0.814	Intermediate Similarity	NPC475211
0.814	Intermediate Similarity	NPC474728
0.8125	Intermediate Similarity	NPC320144
0.8125	Intermediate Similarity	NPC220379
0.8118	Intermediate Similarity	NPC3032
0.8118	Intermediate Similarity	NPC131104
0.8118	Intermediate Similarity	NPC473319
0.8082	Intermediate Similarity	NPC230047
0.8082	Intermediate Similarity	NPC19311
0.8077	Intermediate Similarity	NPC195155
0.8077	Intermediate Similarity	NPC179858
0.8077	Intermediate Similarity	NPC97534
0.8077	Intermediate Similarity	NPC174964
0.8072	Intermediate Similarity	NPC473336
0.8072	Intermediate Similarity	NPC471044
0.8068	Intermediate Similarity	NPC23621
0.8068	Intermediate Similarity	NPC184006
0.8068	Intermediate Similarity	NPC78580
0.8068	Intermediate Similarity	NPC296164
0.8068	Intermediate Similarity	NPC74751
0.8052	Intermediate Similarity	NPC81759
0.8046	Intermediate Similarity	NPC160506
0.8046	Intermediate Similarity	NPC471901
0.8023	Intermediate Similarity	NPC471459
0.8023	Intermediate Similarity	NPC67653
0.8	Intermediate Similarity	NPC329117
0.8	Intermediate Similarity	NPC475977
0.8	Intermediate Similarity	NPC185465
0.8	Intermediate Similarity	NPC162107
0.8	Intermediate Similarity	NPC33768
0.8	Intermediate Similarity	NPC46912
0.7978	Intermediate Similarity	NPC195715
0.7978	Intermediate Similarity	NPC23241
0.7978	Intermediate Similarity	NPC82633
0.7978	Intermediate Similarity	NPC474727
0.7976	Intermediate Similarity	NPC474572
0.7976	Intermediate Similarity	NPC98270
0.7976	Intermediate Similarity	NPC131350
0.7975	Intermediate Similarity	NPC471046
0.7975	Intermediate Similarity	NPC475742
0.7975	Intermediate Similarity	NPC5767
0.7955	Intermediate Similarity	NPC471902
0.7955	Intermediate Similarity	NPC473690
0.7955	Intermediate Similarity	NPC287118
0.7952	Intermediate Similarity	NPC471037
0.7927	Intermediate Similarity	NPC73515
0.7927	Intermediate Similarity	NPC12933
0.7922	Intermediate Similarity	NPC290058
0.7922	Intermediate Similarity	NPC478227
0.7907	Intermediate Similarity	NPC52169
0.7907	Intermediate Similarity	NPC182797
0.7907	Intermediate Similarity	NPC246708
0.7907	Intermediate Similarity	NPC40552
0.7889	Intermediate Similarity	NPC235109
0.7889	Intermediate Similarity	NPC163685
0.7889	Intermediate Similarity	NPC230151
0.7889	Intermediate Similarity	NPC327179
0.7882	Intermediate Similarity	NPC9892
0.7882	Intermediate Similarity	NPC248216
0.7882	Intermediate Similarity	NPC10005
0.7882	Intermediate Similarity	NPC329943
0.7882	Intermediate Similarity	NPC91525
0.7882	Intermediate Similarity	NPC120395
0.7882	Intermediate Similarity	NPC12774
0.7882	Intermediate Similarity	NPC72638
0.7882	Intermediate Similarity	NPC2783
0.7875	Intermediate Similarity	NPC221420
0.7875	Intermediate Similarity	NPC471151
0.7875	Intermediate Similarity	NPC212453
0.7875	Intermediate Similarity	NPC477918
0.7875	Intermediate Similarity	NPC84868
0.7875	Intermediate Similarity	NPC307865
0.7875	Intermediate Similarity	NPC23884
0.7867	Intermediate Similarity	NPC476928
0.7857	Intermediate Similarity	NPC475509
0.7857	Intermediate Similarity	NPC171789
0.7857	Intermediate Similarity	NPC9060
0.7857	Intermediate Similarity	NPC181871
0.7848	Intermediate Similarity	NPC477934
0.7841	Intermediate Similarity	NPC475416
0.7831	Intermediate Similarity	NPC121121
0.7821	Intermediate Similarity	NPC232112
0.7821	Intermediate Similarity	NPC109510
0.7816	Intermediate Similarity	NPC143232
0.7816	Intermediate Similarity	NPC198664
0.7816	Intermediate Similarity	NPC225585
0.7816	Intermediate Similarity	NPC270768
0.7816	Intermediate Similarity	NPC274330
0.7816	Intermediate Similarity	NPC121798
0.7816	Intermediate Similarity	NPC25906
0.7816	Intermediate Similarity	NPC290972
0.7816	Intermediate Similarity	NPC293048
0.7816	Intermediate Similarity	NPC470588
0.7816	Intermediate Similarity	NPC59263
0.7816	Intermediate Similarity	NPC64872
0.7816	Intermediate Similarity	NPC61543
0.7816	Intermediate Similarity	NPC263393
0.7816	Intermediate Similarity	NPC475049
0.7816	Intermediate Similarity	NPC234346
0.7816	Intermediate Similarity	NPC127689
0.7816	Intermediate Similarity	NPC130520
0.7808	Intermediate Similarity	NPC290791
0.7808	Intermediate Similarity	NPC292419
0.7802	Intermediate Similarity	NPC476878
0.7802	Intermediate Similarity	NPC470425
0.7802	Intermediate Similarity	NPC472145
0.7802	Intermediate Similarity	NPC158347
0.7802	Intermediate Similarity	NPC476879
0.7802	Intermediate Similarity	NPC26413
0.7792	Intermediate Similarity	NPC108131
0.7792	Intermediate Similarity	NPC477929
0.7791	Intermediate Similarity	NPC470920
0.7791	Intermediate Similarity	NPC269360
0.7791	Intermediate Similarity	NPC130577
0.7791	Intermediate Similarity	NPC98442
0.7791	Intermediate Similarity	NPC88716
0.7791	Intermediate Similarity	NPC51700
0.7791	Intermediate Similarity	NPC307426
0.7791	Intermediate Similarity	NPC142415

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 NPC31031 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	498
0.1-0.2	3469
0.2-0.3	3433
0.3-0.4	1153
0.4-0.5	299
0.5-0.6	232
0.6-0.7	43
0.7-0.8	23
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
0.8442	Intermediate Similarity	NPD6117	Approved
0.8333	Intermediate Similarity	NPD6116	Phase 1
0.8228	Intermediate Similarity	NPD6118	Approved
0.8228	Intermediate Similarity	NPD6115	Approved
0.8228	Intermediate Similarity	NPD6114	Approved
0.8228	Intermediate Similarity	NPD6697	Approved
0.8182	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7748	Approved
0.8046	Intermediate Similarity	NPD8034	Phase 2
0.8046	Intermediate Similarity	NPD8035	Phase 2
0.7802	Intermediate Similarity	NPD7902	Approved
0.7765	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5777	Approved
0.7662	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD4224	Phase 2
0.7473	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7900	Approved
0.7468	Intermediate Similarity	NPD6081	Approved
0.7407	Intermediate Similarity	NPD3702	Approved
0.7407	Intermediate Similarity	NPD3703	Phase 2
0.7342	Intermediate Similarity	NPD4245	Approved
0.7342	Intermediate Similarity	NPD4244	Approved
0.7308	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5360	Phase 3
0.7215	Intermediate Similarity	NPD3698	Phase 2
0.7125	Intermediate Similarity	NPD4789	Approved
0.6941	Remote Similarity	NPD3671	Phase 1
0.6923	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4758	Discontinued
0.6809	Remote Similarity	NPD6399	Phase 3
0.679	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5364	Discontinued
0.6735	Remote Similarity	NPD8418	Phase 2
0.6712	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7645	Phase 2
0.6634	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7638	Approved
0.6574	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7640	Approved
0.6566	Remote Similarity	NPD7639	Approved
0.6559	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD8133	Approved
0.6436	Remote Similarity	NPD7632	Discontinued
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	NPD6928	Phase 2
0.6375	Remote Similarity	NPD7909	Approved
0.6344	Remote Similarity	NPD3618	Phase 1
0.6344	Remote Similarity	NPD7334	Approved
0.6344	Remote Similarity	NPD7146	Approved
0.6344	Remote Similarity	NPD7521	Approved
0.6344	Remote Similarity	NPD6684	Approved
0.6344	Remote Similarity	NPD5330	Approved
0.6344	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD5328	Approved
0.631	Remote Similarity	NPD4787	Phase 1
0.6304	Remote Similarity	NPD4786	Approved
0.6286	Remote Similarity	NPD6881	Approved
0.6286	Remote Similarity	NPD7320	Approved
0.6286	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6899	Approved
0.6282	Remote Similarity	NPD3198	Approved
0.6277	Remote Similarity	NPD3573	Approved
0.6267	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD3667	Approved
0.6262	Remote Similarity	NPD8130	Phase 1
0.6228	Remote Similarity	NPD8328	Phase 3
0.6226	Remote Similarity	NPD6372	Approved
0.6226	Remote Similarity	NPD6373	Approved
0.6211	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD6903	Approved
0.6211	Remote Similarity	NPD5737	Approved
0.6204	Remote Similarity	NPD8297	Approved
0.62	Remote Similarity	NPD6083	Phase 2
0.62	Remote Similarity	NPD6084	Phase 2
0.6196	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4788	Approved
0.6196	Remote Similarity	NPD3669	Approved
0.619	Remote Similarity	NPD5697	Approved
0.619	Remote Similarity	NPD3726	Approved
0.619	Remote Similarity	NPD5701	Approved
0.619	Remote Similarity	NPD3725	Approved
0.6186	Remote Similarity	NPD6411	Approved
0.6186	Remote Similarity	NPD6079	Approved
0.6168	Remote Similarity	NPD7290	Approved
0.6168	Remote Similarity	NPD7102	Approved
0.6168	Remote Similarity	NPD6883	Approved
0.6154	Remote Similarity	NPD1780	Approved
0.6154	Remote Similarity	NPD1779	Approved
0.6132	Remote Similarity	NPD6011	Approved
0.6122	Remote Similarity	NPD8171	Discontinued
0.6111	Remote Similarity	NPD6847	Approved
0.6111	Remote Similarity	NPD6649	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	NPD2266	Phase 2
0.6111	Remote Similarity	NPD6650	Approved
0.61	Remote Similarity	NPD7732	Phase 3
0.61	Remote Similarity	NPD7614	Phase 1
0.6095	Remote Similarity	NPD6920	Discontinued
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
0.6044	Remote Similarity	NPD7525	Registered
0.6036	Remote Similarity	NPD6940	Discontinued
0.6019	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD4238	Approved
0.6	Remote Similarity	NPD8298	Phase 2
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7115	Discovery
0.598	Remote Similarity	NPD5696	Approved
0.5979	Remote Similarity	NPD6101	Approved
0.5979	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4202	Approved
0.5957	Remote Similarity	NPD3666	Approved
0.5957	Remote Similarity	NPD3668	Phase 3
0.5957	Remote Similarity	NPD3133	Approved
0.5957	Remote Similarity	NPD3665	Phase 1
0.5943	Remote Similarity	NPD8040	Discontinued
0.5941	Remote Similarity	NPD5222	Approved
0.5941	Remote Similarity	NPD4697	Phase 3
0.5941	Remote Similarity	NPD5221	Approved
0.5941	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6868	Approved
0.5889	Remote Similarity	NPD8144	Approved
0.5889	Remote Similarity	NPD8143	Approved
0.5888	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5173	Approved
0.5882	Remote Similarity	NPD4755	Approved
0.5865	Remote Similarity	NPD1700	Approved
0.5844	Remote Similarity	NPD3728	Approved
0.5844	Remote Similarity	NPD3730	Approved
0.5843	Remote Similarity	NPD2257	Approved
0.5833	Remote Similarity	NPD634	Phase 3
0.5833	Remote Similarity	NPD6415	Discontinued
0.5833	Remote Similarity	NPD6098	Approved
0.5833	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD4225	Approved
0.5824	Remote Similarity	NPD3617	Approved
0.5816	Remote Similarity	NPD6080	Approved
0.5816	Remote Similarity	NPD6673	Approved
0.5816	Remote Similarity	NPD6904	Approved
0.5794	Remote Similarity	NPD6008	Approved
0.5789	Remote Similarity	NPD3186	Phase 1
0.5789	Remote Similarity	NPD6335	Approved
0.5769	Remote Similarity	NPD5285	Approved
0.5769	Remote Similarity	NPD4700	Approved
0.5769	Remote Similarity	NPD4696	Approved
0.5769	Remote Similarity	NPD5286	Approved
0.5755	Remote Similarity	NPD7987	Approved
0.5755	Remote Similarity	NPD7986	Approved
0.5755	Remote Similarity	NPD7912	Approved
0.5755	Remote Similarity	NPD7911	Approved
0.5753	Remote Similarity	NPD384	Approved
0.5753	Remote Similarity	NPD385	Approved
0.5752	Remote Similarity	NPD6274	Approved
0.575	Remote Similarity	NPD7736	Approved
0.5741	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6412	Phase 2
0.5739	Remote Similarity	NPD7100	Approved
0.5739	Remote Similarity	NPD7101	Approved
0.5729	Remote Similarity	NPD1694	Approved
0.5714	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4632	Approved
0.5714	Remote Similarity	NPD7507	Approved
0.5714	Remote Similarity	NPD5223	Approved
0.5702	Remote Similarity	NPD6317	Approved
0.5699	Remote Similarity	NPD4695	Discontinued
0.5694	Remote Similarity	NPD2699	Approved
0.5688	Remote Similarity	NPD6686	Approved
0.5686	Remote Similarity	NPD7991	Discontinued
0.566	Remote Similarity	NPD5225	Approved
0.566	Remote Similarity	NPD5224	Approved
0.566	Remote Similarity	NPD4633	Approved
0.566	Remote Similarity	NPD5211	Phase 2
0.566	Remote Similarity	NPD5226	Approved
0.5657	Remote Similarity	NPD4753	Phase 2
0.5652	Remote Similarity	NPD6314	Approved
0.5652	Remote Similarity	NPD6313	Approved
0.5644	Remote Similarity	NPD5779	Approved
0.5644	Remote Similarity	NPD5778	Approved
0.5641	Remote Similarity	NPD6921	Approved
0.5641	Remote Similarity	NPD6908	Approved
0.5641	Remote Similarity	NPD6909	Approved
0.5607	Remote Similarity	NPD5174	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