NPASS Compound

Structure

NPC290614 OpenBabel07101719252D 34 38 0 0 1 0 0 0 0 0999 V2000 3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0186 -0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5058 -1.4615 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 2.5315 2.4359 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 0.0000 0.9744 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 -1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -2.4359 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 1.6876 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 4.2191 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 1 0 0 0 0 0 0 0 0 0 4.2191 0.4872 0.0000 C 0 0 2 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 -1.6876 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 -2.4359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3753 1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0629 -0.0000 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 -0.8438 -1.4615 0.0000 C 0 0 2 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 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 -3.3753 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0629 -0.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9067 0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 27 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 1 0 0 0 19 24 1 0 0 0 0 19 29 1 0 0 0 0 20 26 1 0 0 0 0 20 27 1 6 0 0 0 21 27 1 6 0 0 0 21 30 1 0 0 0 0 22 26 1 0 0 0 0 22 31 1 1 0 0 0 23 28 1 1 0 0 0 23 32 1 0 0 0 0 24 28 1 1 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	5.205
LogD:	4.515
LogS:	-4.095
# 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:	0.405
Synthetic Accessibility Score:	4.936
Fsp3:	0.9
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:	-5.312
MDCK Permeability:	2.2161500965012237e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.841

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.326
Plasma Protein Binding (PPB):	95.12714385986328%
Volume Distribution (VD):	0.686
Pgp-substrate:	3.3388891220092773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.258
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.83
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.716
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	3.06
Half-life (T1/2):	0.355

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.53
Carcinogencity:	0.032
Eye Corrosion:	0.129
Eye Irritation:	0.201
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC290614

Natural Product ID:	NPC290614
*Common Name:**	Triptocallic Acid A
IUPAC Name:	(1R,2R,4S,4aR,6aR,6aS,6bR,8aR,10R,12aR,14bS)-4,10-dihydroxy-1,4a,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-2-carboxylic acid
Synonyms:
Standard InCHIKey:	IWVWTVWLRSUYNC-BDQDAIHRSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-17-18(25(33)34)16-23(32)28(5)14-15-29(6)19(24(17)28)8-9-21-27(4)12-11-22(31)26(2,3)20(27)10-13-30(21,29)7/h8,17-18,20-24,31-32H,9-16H2,1-7H3,(H,33,34)/t17-,18+,20-,21+,22+,23-,24-,27-,28-,29+,30+/m0/s1
SMILES:	OC(=O)[C@@H]1C[C@H](O)[C@]2([C@@H]([C@H]1C)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@H](C1(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485459
PubChem CID:	44575704
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
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	10.6	pg/ml	PMID[506837]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	705.7	pg/ml	PMID[506837]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[506837]

☑ 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 NPC290614 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	208
0.1-0.2	1352
0.2-0.3	4914
0.3-0.4	14148
0.4-0.5	8869
0.5-0.6	5504
0.6-0.7	4740
0.7-0.8	2223
0.8-0.85	380
0.85-0.9	116
0.9-0.95	163
0.95-1	80

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC227467
1.0	High Similarity	NPC7260
1.0	High Similarity	NPC477872
1.0	High Similarity	NPC210037
1.0	High Similarity	NPC18872
1.0	High Similarity	NPC120968
1.0	High Similarity	NPC273621
0.9882	High Similarity	NPC105189
0.9882	High Similarity	NPC187722
0.9881	High Similarity	NPC290972
0.9881	High Similarity	NPC25906
0.9881	High Similarity	NPC64872
0.9767	High Similarity	NPC202728
0.9767	High Similarity	NPC118519
0.9767	High Similarity	NPC229281
0.9767	High Similarity	NPC158059
0.9765	High Similarity	NPC193750
0.9765	High Similarity	NPC291028
0.9765	High Similarity	NPC130278
0.9762	High Similarity	NPC52169
0.9762	High Similarity	NPC182797
0.9655	High Similarity	NPC191412
0.9655	High Similarity	NPC114159
0.9655	High Similarity	NPC6818
0.9651	High Similarity	NPC38754
0.9647	High Similarity	NPC234346
0.9647	High Similarity	NPC130520
0.9647	High Similarity	NPC121798
0.9647	High Similarity	NPC263393
0.9647	High Similarity	NPC274330
0.9647	High Similarity	NPC127689
0.9647	High Similarity	NPC61543
0.9647	High Similarity	NPC293048
0.9647	High Similarity	NPC198664
0.9647	High Similarity	NPC143232
0.9647	High Similarity	NPC225585
0.9647	High Similarity	NPC59263
0.9647	High Similarity	NPC270768
0.9643	High Similarity	NPC171203
0.9643	High Similarity	NPC102683
0.9643	High Similarity	NPC51700
0.9643	High Similarity	NPC88716
0.9643	High Similarity	NPC142415
0.9643	High Similarity	NPC242468
0.9643	High Similarity	NPC68160
0.9643	High Similarity	NPC18064
0.9643	High Similarity	NPC293564
0.9643	High Similarity	NPC98442
0.9643	High Similarity	NPC307426
0.9643	High Similarity	NPC130577
0.9545	High Similarity	NPC96916
0.954	High Similarity	NPC118490
0.9535	High Similarity	NPC111110
0.9535	High Similarity	NPC470589
0.9535	High Similarity	NPC126369
0.9529	High Similarity	NPC474512
0.9529	High Similarity	NPC181225
0.9529	High Similarity	NPC473242
0.9529	High Similarity	NPC40552
0.9529	High Similarity	NPC17733
0.9529	High Similarity	NPC246708
0.9529	High Similarity	NPC470629
0.9529	High Similarity	NPC290690
0.9524	High Similarity	NPC72638
0.9438	High Similarity	NPC132824
0.9438	High Similarity	NPC327179
0.9438	High Similarity	NPC204961
0.9438	High Similarity	NPC158371
0.9438	High Similarity	NPC259733
0.9438	High Similarity	NPC73004
0.9438	High Similarity	NPC157113
0.9438	High Similarity	NPC173744
0.9438	High Similarity	NPC207922
0.9438	High Similarity	NPC62516
0.9438	High Similarity	NPC116457
0.9432	High Similarity	NPC20235
0.9432	High Similarity	NPC32407
0.9432	High Similarity	NPC231063
0.9432	High Similarity	NPC145667
0.9432	High Similarity	NPC60692
0.9432	High Similarity	NPC282395
0.9432	High Similarity	NPC88116
0.9432	High Similarity	NPC263548
0.9432	High Similarity	NPC299996
0.9425	High Similarity	NPC84319
0.9425	High Similarity	NPC158030
0.9425	High Similarity	NPC25299
0.9425	High Similarity	NPC288833
0.9425	High Similarity	NPC233455
0.9425	High Similarity	NPC4036
0.9425	High Similarity	NPC306541
0.9425	High Similarity	NPC145067
0.9425	High Similarity	NPC472149
0.9425	High Similarity	NPC324341
0.9425	High Similarity	NPC474525
0.9425	High Similarity	NPC966
0.9425	High Similarity	NPC65120
0.9425	High Similarity	NPC282616
0.9425	High Similarity	NPC235884
0.9425	High Similarity	NPC52021
0.9425	High Similarity	NPC155120
0.9425	High Similarity	NPC228784
0.9425	High Similarity	NPC71074
0.9425	High Similarity	NPC300351
0.9419	High Similarity	NPC474972
0.9419	High Similarity	NPC470588
0.9419	High Similarity	NPC95246
0.9419	High Similarity	NPC161751
0.9333	High Similarity	NPC261935
0.9333	High Similarity	NPC259788
0.9333	High Similarity	NPC9613
0.9333	High Similarity	NPC43686
0.9333	High Similarity	NPC247139
0.9333	High Similarity	NPC106112
0.9333	High Similarity	NPC255589
0.9333	High Similarity	NPC187933
0.9326	High Similarity	NPC290481
0.9326	High Similarity	NPC139570
0.9326	High Similarity	NPC83693
0.9326	High Similarity	NPC473240
0.9318	High Similarity	NPC275809
0.9318	High Similarity	NPC74855
0.9318	High Similarity	NPC307335
0.9318	High Similarity	NPC63118
0.9318	High Similarity	NPC86368
0.9318	High Similarity	NPC295643
0.9318	High Similarity	NPC298554
0.9318	High Similarity	NPC49776
0.9318	High Similarity	NPC272075
0.9318	High Similarity	NPC214756
0.9318	High Similarity	NPC136313
0.9318	High Similarity	NPC474436
0.931	High Similarity	NPC172361
0.931	High Similarity	NPC113989
0.931	High Similarity	NPC46441
0.931	High Similarity	NPC120840
0.931	High Similarity	NPC86372
0.931	High Similarity	NPC49320
0.931	High Similarity	NPC474728
0.9294	High Similarity	NPC74363
0.9294	High Similarity	NPC475862
0.9231	High Similarity	NPC29765
0.9231	High Similarity	NPC174663
0.9231	High Similarity	NPC271614
0.9231	High Similarity	NPC111214
0.9231	High Similarity	NPC164349
0.9222	High Similarity	NPC305464
0.9222	High Similarity	NPC25848
0.9222	High Similarity	NPC476318
0.9222	High Similarity	NPC476327
0.9222	High Similarity	NPC19376
0.9222	High Similarity	NPC201657
0.9222	High Similarity	NPC307282
0.9213	High Similarity	NPC474529
0.9213	High Similarity	NPC91010
0.9213	High Similarity	NPC159365
0.9213	High Similarity	NPC148964
0.9213	High Similarity	NPC209868
0.9213	High Similarity	NPC222047
0.9205	High Similarity	NPC77099
0.9205	High Similarity	NPC285184
0.9205	High Similarity	NPC471588
0.9205	High Similarity	NPC60755
0.9205	High Similarity	NPC475708
0.9205	High Similarity	NPC6255
0.9205	High Similarity	NPC470590
0.9195	High Similarity	NPC30522
0.9195	High Similarity	NPC474686
0.9186	High Similarity	NPC71507
0.9186	High Similarity	NPC73064
0.9176	High Similarity	NPC133954
0.913	High Similarity	NPC35239
0.9121	High Similarity	NPC203343
0.9121	High Similarity	NPC312075
0.9121	High Similarity	NPC189880
0.9111	High Similarity	NPC474727
0.9111	High Similarity	NPC198245
0.9111	High Similarity	NPC32118
0.9111	High Similarity	NPC148523
0.9101	High Similarity	NPC474806
0.9101	High Similarity	NPC133579
0.907	High Similarity	NPC213412
0.907	High Similarity	NPC95594
0.907	High Similarity	NPC477579
0.907	High Similarity	NPC73038
0.907	High Similarity	NPC235341
0.9059	High Similarity	NPC171789
0.9032	High Similarity	NPC118964
0.9032	High Similarity	NPC233012
0.9032	High Similarity	NPC256247
0.9032	High Similarity	NPC54909
0.9022	High Similarity	NPC188833
0.9022	High Similarity	NPC471966
0.9022	High Similarity	NPC260149
0.9022	High Similarity	NPC58942
0.9011	High Similarity	NPC98874
0.9011	High Similarity	NPC230151
0.9	High Similarity	NPC23621
0.9	High Similarity	NPC78580
0.9	High Similarity	NPC80365

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 NPC290614 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1704
0.2-0.3	3828
0.3-0.4	2277
0.4-0.5	696
0.5-0.6	206
0.6-0.7	180
0.7-0.8	66
0.8-0.85	3
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9425	High Similarity	NPD7515	Phase 2
0.9121	High Similarity	NPD7902	Approved
0.9	High Similarity	NPD7748	Approved
0.8791	High Similarity	NPD7901	Clinical (unspecified phase)
0.8791	High Similarity	NPD7900	Approved
0.8523	High Similarity	NPD7520	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD8034	Phase 2
0.837	Intermediate Similarity	NPD8035	Phase 2
0.828	Intermediate Similarity	NPD6399	Phase 3
0.8256	Intermediate Similarity	NPD7645	Phase 2
0.8222	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD4786	Approved
0.7978	Intermediate Similarity	NPD3667	Approved
0.7957	Intermediate Similarity	NPD5328	Approved
0.7789	Intermediate Similarity	NPD6079	Approved
0.7766	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7525	Registered
0.7745	Intermediate Similarity	NPD6675	Approved
0.7745	Intermediate Similarity	NPD5739	Approved
0.7745	Intermediate Similarity	NPD7128	Approved
0.7745	Intermediate Similarity	NPD6402	Approved
0.7708	Intermediate Similarity	NPD4202	Approved
0.7692	Intermediate Similarity	NPD6372	Approved
0.7692	Intermediate Similarity	NPD6373	Approved
0.7677	Intermediate Similarity	NPD7638	Approved
0.766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD4697	Phase 3
0.7614	Intermediate Similarity	NPD6116	Phase 1
0.7609	Intermediate Similarity	NPD3665	Phase 1
0.7609	Intermediate Similarity	NPD3133	Approved
0.7609	Intermediate Similarity	NPD3666	Approved
0.76	Intermediate Similarity	NPD7640	Approved
0.76	Intermediate Similarity	NPD7639	Approved
0.7596	Intermediate Similarity	NPD6881	Approved
0.7596	Intermediate Similarity	NPD7320	Approved
0.7596	Intermediate Similarity	NPD6899	Approved
0.7576	Intermediate Similarity	NPD4755	Approved
0.7547	Intermediate Similarity	NPD6650	Approved
0.7547	Intermediate Similarity	NPD6649	Approved
0.7524	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD6117	Approved
0.75	Intermediate Similarity	NPD5697	Approved
0.7475	Intermediate Similarity	NPD5221	Approved
0.7475	Intermediate Similarity	NPD5222	Approved
0.7475	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7102	Approved
0.7453	Intermediate Similarity	NPD6883	Approved
0.7453	Intermediate Similarity	NPD7290	Approved
0.7447	Intermediate Similarity	NPD6684	Approved
0.7447	Intermediate Similarity	NPD7334	Approved
0.7447	Intermediate Similarity	NPD7146	Approved
0.7447	Intermediate Similarity	NPD6409	Approved
0.7447	Intermediate Similarity	NPD5330	Approved
0.7447	Intermediate Similarity	NPD7521	Approved
0.7434	Intermediate Similarity	NPD8328	Phase 3
0.7429	Intermediate Similarity	NPD6011	Approved
0.7426	Intermediate Similarity	NPD4696	Approved
0.7426	Intermediate Similarity	NPD4700	Approved
0.7426	Intermediate Similarity	NPD5285	Approved
0.7426	Intermediate Similarity	NPD5286	Approved
0.7423	Intermediate Similarity	NPD6411	Approved
0.7419	Intermediate Similarity	NPD3668	Phase 3
0.74	Intermediate Similarity	NPD6083	Phase 2
0.74	Intermediate Similarity	NPD5173	Approved
0.74	Intermediate Similarity	NPD6084	Phase 2
0.7383	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6847	Approved
0.7383	Intermediate Similarity	NPD6617	Approved
0.7383	Intermediate Similarity	NPD6869	Approved
0.7383	Intermediate Similarity	NPD8130	Phase 1
0.7368	Intermediate Similarity	NPD3573	Approved
0.7364	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6012	Approved
0.7358	Intermediate Similarity	NPD6014	Approved
0.7358	Intermediate Similarity	NPD6013	Approved
0.7353	Intermediate Similarity	NPD5223	Approved
0.7333	Intermediate Similarity	NPD6114	Approved
0.7333	Intermediate Similarity	NPD6697	Approved
0.7333	Intermediate Similarity	NPD6115	Approved
0.7333	Intermediate Similarity	NPD6118	Approved
0.7315	Intermediate Similarity	NPD8297	Approved
0.7315	Intermediate Similarity	NPD6882	Approved
0.73	Intermediate Similarity	NPD7614	Phase 1
0.7292	Intermediate Similarity	NPD6672	Approved
0.7292	Intermediate Similarity	NPD6903	Approved
0.7292	Intermediate Similarity	NPD5737	Approved
0.7282	Intermediate Similarity	NPD5225	Approved
0.7282	Intermediate Similarity	NPD5211	Phase 2
0.7282	Intermediate Similarity	NPD4633	Approved
0.7282	Intermediate Similarity	NPD5224	Approved
0.7282	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5284	Approved
0.7245	Intermediate Similarity	NPD5281	Approved
0.7216	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4753	Phase 2
0.7216	Intermediate Similarity	NPD6101	Approved
0.7212	Intermediate Similarity	NPD4754	Approved
0.7212	Intermediate Similarity	NPD5175	Approved
0.7212	Intermediate Similarity	NPD5174	Approved
0.7207	Intermediate Similarity	NPD7115	Discovery
0.72	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6942	Approved
0.7191	Intermediate Similarity	NPD7339	Approved
0.7174	Intermediate Similarity	NPD4695	Discontinued
0.7157	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD5141	Approved
0.7111	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4632	Approved
0.7083	Intermediate Similarity	NPD5279	Phase 3
0.7075	Intermediate Similarity	NPD4767	Approved
0.7075	Intermediate Similarity	NPD6008	Approved
0.7075	Intermediate Similarity	NPD4768	Approved
0.703	Intermediate Similarity	NPD5210	Approved
0.703	Intermediate Similarity	NPD5695	Phase 3
0.703	Intermediate Similarity	NPD4629	Approved
0.7021	Intermediate Similarity	NPD4223	Phase 3
0.7021	Intermediate Similarity	NPD4221	Approved
0.7009	Intermediate Similarity	NPD6412	Phase 2
0.6991	Remote Similarity	NPD6335	Approved
0.699	Remote Similarity	NPD4225	Approved
0.6979	Remote Similarity	NPD5329	Approved
0.6964	Remote Similarity	NPD6868	Approved
0.6964	Remote Similarity	NPD6274	Approved
0.6961	Remote Similarity	NPD7732	Phase 3
0.6952	Remote Similarity	NPD7632	Discontinued
0.6947	Remote Similarity	NPD4788	Approved
0.6944	Remote Similarity	NPD5128	Approved
0.6944	Remote Similarity	NPD4730	Approved
0.6944	Remote Similarity	NPD4729	Approved
0.693	Remote Similarity	NPD7101	Approved
0.693	Remote Similarity	NPD7100	Approved
0.6907	Remote Similarity	NPD6098	Approved
0.6903	Remote Similarity	NPD6317	Approved
0.6903	Remote Similarity	NPD6009	Approved
0.6881	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4197	Approved
0.6869	Remote Similarity	NPD6673	Approved
0.6869	Remote Similarity	NPD6904	Approved
0.6869	Remote Similarity	NPD6080	Approved
0.6854	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6313	Approved
0.6842	Remote Similarity	NPD6314	Approved
0.6842	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5779	Approved
0.6832	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5251	Approved
0.6818	Remote Similarity	NPD4634	Approved
0.6818	Remote Similarity	NPD5247	Approved
0.6818	Remote Similarity	NPD5135	Approved
0.6818	Remote Similarity	NPD5248	Approved
0.6818	Remote Similarity	NPD5249	Phase 3
0.6818	Remote Similarity	NPD5250	Approved
0.6818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5169	Approved
0.6818	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6908	Approved
0.681	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6909	Approved
0.6804	Remote Similarity	NPD1694	Approved
0.6789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5168	Approved
0.6789	Remote Similarity	NPD6686	Approved
0.6786	Remote Similarity	NPD8133	Approved
0.6774	Remote Similarity	NPD3617	Approved
0.6774	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6001	Approved
0.6757	Remote Similarity	NPD5217	Approved
0.6757	Remote Similarity	NPD5216	Approved
0.6757	Remote Similarity	NPD5215	Approved
0.6757	Remote Similarity	NPD5127	Approved
0.675	Remote Similarity	NPD7736	Approved
0.6735	Remote Similarity	NPD4693	Phase 3
0.6735	Remote Similarity	NPD4689	Approved
0.6735	Remote Similarity	NPD4688	Approved
0.6735	Remote Similarity	NPD4138	Approved
0.6735	Remote Similarity	NPD4623	Approved
0.6735	Remote Similarity	NPD4690	Approved
0.6735	Remote Similarity	NPD5205	Approved
0.6735	Remote Similarity	NPD4519	Discontinued
0.6724	Remote Similarity	NPD6319	Approved
0.6723	Remote Similarity	NPD7507	Approved
0.6695	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD7492	Approved
0.6632	Remote Similarity	NPD5368	Approved
0.6632	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3703	Phase 2
0.66	Remote Similarity	NPD5208	Approved
0.6583	Remote Similarity	NPD6336	Discontinued
0.6583	Remote Similarity	NPD6616	Approved
0.6581	Remote Similarity	NPD6059	Approved
0.6581	Remote Similarity	NPD6054	Approved
0.6579	Remote Similarity	NPD5167	Approved
0.6569	Remote Similarity	NPD5693	Phase 1

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