NPASS Compound

Structure

CID102414 OpenBabel06191715452D 33 36 0 0 1 0 0 0 0 0999 V2000 0.0789 6.5794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4621 5.8928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3779 -2.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2526 -2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 0.5236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6692 4.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0970 4.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2728 3.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -1.4622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6894 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6879 0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6885 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2210 -0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3770 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8440 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4934 5.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 2.4357 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8448 1.4617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6888 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 -0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5336 -1.4618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2212 -1.4613 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8138 2.5372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3776 -1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5333 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0874 -1.9610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2102 3.4269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3861 1.7490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 23 2 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 22 2 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 29 1 6 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 6 0 0 0 25 27 1 0 0 0 0 25 31 1 6 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	509.035
LogP:	6.607
LogD:	4.863
LogS:	-4.73
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	4.86
Fsp3:	0.767
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:	-5.167
MDCK Permeability:	2.3730510292807594e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.711
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	94.5315933227539%
Volume Distribution (VD):	0.952
Pgp-substrate:	2.8424224853515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.195
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.311
CYP3A4-inhibitor:	0.103
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	4.436
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.811
Drug-inuced Liver Injury (DILI):	0.004
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.958
Carcinogencity:	0.218
Eye Corrosion:	0.006
Eye Irritation:	0.053
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: NPC102414

Natural Product ID:	NPC102414
*Common Name:**	3-Epidehydrotrametenolic Acid
IUPAC Name:	2-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms:	3-Epidehydrotrametenolic Acid
Standard InCHIKey:	QFPLAAZRZNKRRY-FHZHDSSISA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,11,14,20-21,24-25,31H,8,10,12-13,15-18H2,1-7H3,(H,32,33)/t20?,21-,24+,25+,28-,29-,30+/m1/s1
SMILES:	CC(=CCCC([C@H]1CC[C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226995
PubChem CID:	12133286
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
NPO33546	Poria coco	Species		Eukaryota	n.a.	Yunnan, Kunming, China	n.a.	PMID[17488130]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[468384]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	9.2	%	PMID[468384]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	45.3	%	PMID[468384]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	79.1	%	PMID[468384]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	100.0	%	PMID[468384]

☑ 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 NPC102414 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	161
0.1-0.2	871
0.2-0.3	4503
0.3-0.4	14016
0.4-0.5	9085
0.5-0.6	6666
0.6-0.7	5008
0.7-0.8	2009
0.8-0.85	266
0.85-0.9	75
0.9-0.95	28
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC77168
1.0	High Similarity	NPC84271
0.9759	High Similarity	NPC187376
0.9759	High Similarity	NPC159046
0.9759	High Similarity	NPC233836
0.9639	High Similarity	NPC28252
0.9639	High Similarity	NPC55309
0.954	High Similarity	NPC469406
0.9524	High Similarity	NPC474684
0.9524	High Similarity	NPC142361
0.9432	High Similarity	NPC162001
0.9432	High Similarity	NPC222845
0.9432	High Similarity	NPC45324
0.9412	High Similarity	NPC242864
0.9302	High Similarity	NPC475921
0.9302	High Similarity	NPC474704
0.9195	High Similarity	NPC175628
0.9195	High Similarity	NPC111585
0.9195	High Similarity	NPC469400
0.9195	High Similarity	NPC148414
0.9176	High Similarity	NPC94755
0.9176	High Similarity	NPC155011
0.9121	High Similarity	NPC186810
0.9121	High Similarity	NPC477813
0.9121	High Similarity	NPC48647
0.9101	High Similarity	NPC49670
0.9091	High Similarity	NPC23434
0.9091	High Similarity	NPC26888
0.9091	High Similarity	NPC297265
0.9091	High Similarity	NPC189520
0.908	High Similarity	NPC474889
0.9048	High Similarity	NPC69279
0.9048	High Similarity	NPC83569
0.8989	High Similarity	NPC470224
0.8989	High Similarity	NPC152897
0.8989	High Similarity	NPC470376
0.8989	High Similarity	NPC66429
0.8989	High Similarity	NPC470375
0.8977	High Similarity	NPC471896
0.8966	High Similarity	NPC471722
0.8953	High Similarity	NPC72133
0.8941	High Similarity	NPC165064
0.8901	High Similarity	NPC173272
0.8889	High Similarity	NPC166906
0.8876	High Similarity	NPC212948
0.8876	High Similarity	NPC86266
0.8876	High Similarity	NPC110657
0.8876	High Similarity	NPC301244
0.8876	High Similarity	NPC212301
0.8864	High Similarity	NPC86319
0.8864	High Similarity	NPC474972
0.8864	High Similarity	NPC161751
0.8864	High Similarity	NPC275740
0.8864	High Similarity	NPC95246
0.8864	High Similarity	NPC128496
0.881	High Similarity	NPC201912
0.881	High Similarity	NPC473420
0.881	High Similarity	NPC38350
0.8791	High Similarity	NPC470016
0.8791	High Similarity	NPC69548
0.8791	High Similarity	NPC48330
0.8791	High Similarity	NPC317586
0.8791	High Similarity	NPC263347
0.8791	High Similarity	NPC184848
0.8778	High Similarity	NPC170220
0.8778	High Similarity	NPC141497
0.8778	High Similarity	NPC477855
0.8778	High Similarity	NPC214697
0.8778	High Similarity	NPC107674
0.8764	High Similarity	NPC46281
0.8764	High Similarity	NPC191684
0.8764	High Similarity	NPC20388
0.875	High Similarity	NPC48866
0.875	High Similarity	NPC247406
0.875	High Similarity	NPC143767
0.875	High Similarity	NPC471724
0.875	High Similarity	NPC131470
0.8736	High Similarity	NPC325594
0.8736	High Similarity	NPC73038
0.8736	High Similarity	NPC89077
0.8721	High Similarity	NPC473246
0.8721	High Similarity	NPC59453
0.8721	High Similarity	NPC221758
0.8706	High Similarity	NPC73882
0.8706	High Similarity	NPC260956
0.8696	High Similarity	NPC328162
0.8696	High Similarity	NPC305483
0.8696	High Similarity	NPC120708
0.8696	High Similarity	NPC96859
0.8696	High Similarity	NPC155676
0.8681	High Similarity	NPC80365
0.8675	High Similarity	NPC186191
0.8675	High Similarity	NPC205455
0.8652	High Similarity	NPC54689
0.8652	High Similarity	NPC474686
0.8646	High Similarity	NPC477812
0.8636	High Similarity	NPC18064
0.8636	High Similarity	NPC141292
0.8636	High Similarity	NPC102683
0.8636	High Similarity	NPC475740
0.8636	High Similarity	NPC88716
0.8636	High Similarity	NPC98442
0.8636	High Similarity	NPC96496
0.8636	High Similarity	NPC51700
0.8636	High Similarity	NPC312215
0.8636	High Similarity	NPC142415
0.8636	High Similarity	NPC171203
0.8636	High Similarity	NPC136548
0.8636	High Similarity	NPC475772
0.8636	High Similarity	NPC293564
0.8636	High Similarity	NPC71507
0.8636	High Similarity	NPC130577
0.8636	High Similarity	NPC242468
0.8636	High Similarity	NPC68160
0.8636	High Similarity	NPC307426
0.8621	High Similarity	NPC474083
0.8621	High Similarity	NPC294438
0.8621	High Similarity	NPC264317
0.8621	High Similarity	NPC470574
0.8602	High Similarity	NPC320306
0.8602	High Similarity	NPC108078
0.8588	High Similarity	NPC147066
0.8587	High Similarity	NPC127063
0.8587	High Similarity	NPC279974
0.8587	High Similarity	NPC88310
0.8571	High Similarity	NPC274996
0.8571	High Similarity	NPC69454
0.8571	High Similarity	NPC134826
0.8571	High Similarity	NPC477371
0.8571	High Similarity	NPC196827
0.8556	High Similarity	NPC69622
0.8556	High Similarity	NPC183283
0.8556	High Similarity	NPC44240
0.8556	High Similarity	NPC123854
0.8554	High Similarity	NPC214570
0.8539	High Similarity	NPC52169
0.8539	High Similarity	NPC24816
0.8539	High Similarity	NPC472220
0.8539	High Similarity	NPC193360
0.8539	High Similarity	NPC292491
0.8539	High Similarity	NPC40552
0.8539	High Similarity	NPC17733
0.8539	High Similarity	NPC97884
0.8539	High Similarity	NPC310752
0.8539	High Similarity	NPC44181
0.8539	High Similarity	NPC181225
0.8539	High Similarity	NPC470629
0.8539	High Similarity	NPC294480
0.8539	High Similarity	NPC328539
0.8539	High Similarity	NPC290690
0.8539	High Similarity	NPC182797
0.8539	High Similarity	NPC246708
0.8539	High Similarity	NPC473242
0.8539	High Similarity	NPC474512
0.8523	High Similarity	NPC222613
0.8523	High Similarity	NPC474778
0.8523	High Similarity	NPC474733
0.8523	High Similarity	NPC72638
0.8523	High Similarity	NPC12774
0.8523	High Similarity	NPC474970
0.8523	High Similarity	NPC212843
0.8523	High Similarity	NPC118648
0.8523	High Similarity	NPC145879
0.8523	High Similarity	NPC473168
0.8523	High Similarity	NPC51014
0.8523	High Similarity	NPC475022
0.8523	High Similarity	NPC31564
0.8523	High Similarity	NPC474732
0.8523	High Similarity	NPC2783
0.8511	High Similarity	NPC166745
0.8511	High Similarity	NPC235464
0.8511	High Similarity	NPC471717
0.8506	High Similarity	NPC82902
0.8506	High Similarity	NPC85774
0.8506	High Similarity	NPC214043
0.8506	High Similarity	NPC171789
0.8495	Intermediate Similarity	NPC472941
0.8495	Intermediate Similarity	NPC471153
0.8495	Intermediate Similarity	NPC456
0.8495	Intermediate Similarity	NPC301534
0.8495	Intermediate Similarity	NPC250757
0.8488	Intermediate Similarity	NPC151519
0.8488	Intermediate Similarity	NPC296367
0.8488	Intermediate Similarity	NPC201852
0.8488	Intermediate Similarity	NPC202389
0.8478	Intermediate Similarity	NPC209662
0.8478	Intermediate Similarity	NPC159410
0.8478	Intermediate Similarity	NPC471720
0.8462	Intermediate Similarity	NPC45269
0.8462	Intermediate Similarity	NPC272746
0.8462	Intermediate Similarity	NPC63748
0.8462	Intermediate Similarity	NPC154101
0.8462	Intermediate Similarity	NPC233116
0.8452	Intermediate Similarity	NPC318136
0.8452	Intermediate Similarity	NPC275910
0.8444	Intermediate Similarity	NPC263393
0.8444	Intermediate Similarity	NPC225585
0.8444	Intermediate Similarity	NPC293048
0.8444	Intermediate Similarity	NPC61543
0.8444	Intermediate Similarity	NPC214387

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 NPC102414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1209
0.2-0.3	3886
0.3-0.4	2637
0.4-0.5	740
0.5-0.6	222
0.6-0.7	156
0.7-0.8	147
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8721	High Similarity	NPD4786	Approved
0.8652	High Similarity	NPD5328	Approved
0.8621	High Similarity	NPD7520	Clinical (unspecified phase)
0.8523	High Similarity	NPD5279	Phase 3
0.8523	High Similarity	NPD3618	Phase 1
0.8488	Intermediate Similarity	NPD3667	Approved
0.8462	Intermediate Similarity	NPD6079	Approved
0.837	Intermediate Similarity	NPD6399	Phase 3
0.8261	Intermediate Similarity	NPD7515	Phase 2
0.8172	Intermediate Similarity	NPD4202	Approved
0.809	Intermediate Similarity	NPD3666	Approved
0.809	Intermediate Similarity	NPD3133	Approved
0.809	Intermediate Similarity	NPD3665	Phase 1
0.8065	Intermediate Similarity	NPD5281	Approved
0.8065	Intermediate Similarity	NPD5284	Approved
0.8	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD5739	Approved
0.8	Intermediate Similarity	NPD7128	Approved
0.7917	Intermediate Similarity	NPD5222	Approved
0.7917	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4697	Phase 3
0.7917	Intermediate Similarity	NPD5221	Approved
0.7912	Intermediate Similarity	NPD6409	Approved
0.7912	Intermediate Similarity	NPD5330	Approved
0.7912	Intermediate Similarity	NPD7146	Approved
0.7912	Intermediate Similarity	NPD6684	Approved
0.7912	Intermediate Similarity	NPD4694	Approved
0.7912	Intermediate Similarity	NPD7334	Approved
0.7912	Intermediate Similarity	NPD5280	Approved
0.7912	Intermediate Similarity	NPD7521	Approved
0.7895	Intermediate Similarity	NPD7748	Approved
0.7882	Intermediate Similarity	NPD7339	Approved
0.7882	Intermediate Similarity	NPD6942	Approved
0.7872	Intermediate Similarity	NPD8034	Phase 2
0.7872	Intermediate Similarity	NPD6411	Approved
0.7872	Intermediate Similarity	NPD8035	Phase 2
0.7843	Intermediate Similarity	NPD6899	Approved
0.7843	Intermediate Similarity	NPD7320	Approved
0.7843	Intermediate Similarity	NPD6881	Approved
0.7841	Intermediate Similarity	NPD7525	Registered
0.7835	Intermediate Similarity	NPD5173	Approved
0.7835	Intermediate Similarity	NPD6084	Phase 2
0.7835	Intermediate Similarity	NPD6083	Phase 2
0.7835	Intermediate Similarity	NPD4755	Approved
0.7812	Intermediate Similarity	NPD5695	Phase 3
0.7791	Intermediate Similarity	NPD6117	Approved
0.7767	Intermediate Similarity	NPD6372	Approved
0.7767	Intermediate Similarity	NPD6373	Approved
0.7765	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7638	Approved
0.7745	Intermediate Similarity	NPD5701	Approved
0.7745	Intermediate Similarity	NPD5697	Approved
0.7742	Intermediate Similarity	NPD6672	Approved
0.7742	Intermediate Similarity	NPD6903	Approved
0.7742	Intermediate Similarity	NPD5737	Approved
0.7742	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6116	Phase 1
0.7692	Intermediate Similarity	NPD7102	Approved
0.7692	Intermediate Similarity	NPD3668	Phase 3
0.7692	Intermediate Similarity	NPD6883	Approved
0.7692	Intermediate Similarity	NPD7290	Approved
0.7684	Intermediate Similarity	NPD6050	Approved
0.7677	Intermediate Similarity	NPD7640	Approved
0.7677	Intermediate Similarity	NPD7639	Approved
0.7677	Intermediate Similarity	NPD5286	Approved
0.7677	Intermediate Similarity	NPD4700	Approved
0.7677	Intermediate Similarity	NPD4696	Approved
0.7677	Intermediate Similarity	NPD5285	Approved
0.767	Intermediate Similarity	NPD6011	Approved
0.7667	Intermediate Similarity	NPD4221	Approved
0.7667	Intermediate Similarity	NPD4223	Phase 3
0.766	Intermediate Similarity	NPD4753	Phase 2
0.766	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6101	Approved
0.7653	Intermediate Similarity	NPD7902	Approved
0.7619	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6649	Approved
0.7619	Intermediate Similarity	NPD6847	Approved
0.7619	Intermediate Similarity	NPD6617	Approved
0.7619	Intermediate Similarity	NPD6869	Approved
0.7619	Intermediate Similarity	NPD6650	Approved
0.7619	Intermediate Similarity	NPD8130	Phase 1
0.7614	Intermediate Similarity	NPD6697	Approved
0.7614	Intermediate Similarity	NPD6118	Approved
0.7614	Intermediate Similarity	NPD6115	Approved
0.7614	Intermediate Similarity	NPD6114	Approved
0.7609	Intermediate Similarity	NPD5329	Approved
0.76	Intermediate Similarity	NPD5223	Approved
0.7596	Intermediate Similarity	NPD6013	Approved
0.7596	Intermediate Similarity	NPD6012	Approved
0.7596	Intermediate Similarity	NPD6014	Approved
0.7586	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5692	Phase 3
0.7579	Intermediate Similarity	NPD5207	Approved
0.7558	Intermediate Similarity	NPD6926	Approved
0.7558	Intermediate Similarity	NPD6924	Approved
0.7558	Intermediate Similarity	NPD5733	Approved
0.7547	Intermediate Similarity	NPD8297	Approved
0.7547	Intermediate Similarity	NPD6882	Approved
0.7527	Intermediate Similarity	NPD5690	Phase 2
0.7527	Intermediate Similarity	NPD6098	Approved
0.7525	Intermediate Similarity	NPD5224	Approved
0.7525	Intermediate Similarity	NPD5211	Phase 2
0.7525	Intermediate Similarity	NPD5225	Approved
0.7525	Intermediate Similarity	NPD5226	Approved
0.7525	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD4197	Approved
0.75	Intermediate Similarity	NPD6404	Discontinued
0.75	Intermediate Similarity	NPD5694	Approved
0.7474	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5175	Approved
0.7451	Intermediate Similarity	NPD5174	Approved
0.7451	Intermediate Similarity	NPD4754	Approved
0.7449	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5696	Approved
0.7396	Intermediate Similarity	NPD4096	Approved
0.7391	Intermediate Similarity	NPD4788	Approved
0.7386	Intermediate Similarity	NPD6933	Approved
0.7379	Intermediate Similarity	NPD5141	Approved
0.7363	Intermediate Similarity	NPD4692	Approved
0.7363	Intermediate Similarity	NPD4139	Approved
0.7356	Intermediate Similarity	NPD4687	Approved
0.7347	Intermediate Similarity	NPD7900	Approved
0.7347	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4693	Phase 3
0.734	Intermediate Similarity	NPD4690	Approved
0.734	Intermediate Similarity	NPD4138	Approved
0.734	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4689	Approved
0.734	Intermediate Similarity	NPD5205	Approved
0.734	Intermediate Similarity	NPD4688	Approved
0.7339	Intermediate Similarity	NPD6868	Approved
0.7333	Intermediate Similarity	NPD7645	Phase 2
0.7326	Intermediate Similarity	NPD7151	Approved
0.7326	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5276	Approved
0.7326	Intermediate Similarity	NPD7152	Approved
0.7326	Intermediate Similarity	NPD7150	Approved
0.7326	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4632	Approved
0.7308	Intermediate Similarity	NPD4767	Approved
0.7308	Intermediate Similarity	NPD4768	Approved
0.7294	Intermediate Similarity	NPD6922	Approved
0.7294	Intermediate Similarity	NPD6923	Approved
0.7292	Intermediate Similarity	NPD6904	Approved
0.7292	Intermediate Similarity	NPD6673	Approved
0.7292	Intermediate Similarity	NPD6080	Approved
0.7273	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD5210	Approved
0.7273	Intermediate Similarity	NPD4629	Approved
0.7253	Intermediate Similarity	NPD4748	Discontinued
0.7245	Intermediate Similarity	NPD5133	Approved
0.7245	Intermediate Similarity	NPD5778	Approved
0.7245	Intermediate Similarity	NPD5779	Approved
0.7222	Intermediate Similarity	NPD3617	Approved
0.7209	Intermediate Similarity	NPD7144	Approved
0.7209	Intermediate Similarity	NPD7143	Approved
0.7207	Intermediate Similarity	NPD6335	Approved
0.7188	Intermediate Similarity	NPD5208	Approved
0.7188	Intermediate Similarity	NPD4518	Approved
0.7182	Intermediate Similarity	NPD6274	Approved
0.7172	Intermediate Similarity	NPD6001	Approved
0.717	Intermediate Similarity	NPD4730	Approved
0.717	Intermediate Similarity	NPD5128	Approved
0.717	Intermediate Similarity	NPD4729	Approved
0.717	Intermediate Similarity	NPD5168	Approved
0.7143	Intermediate Similarity	NPD6929	Approved
0.7143	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD7100	Approved
0.7143	Intermediate Similarity	NPD7101	Approved
0.7126	Intermediate Similarity	NPD4243	Approved
0.7117	Intermediate Similarity	NPD6317	Approved
0.7117	Intermediate Similarity	NPD6009	Approved
0.71	Intermediate Similarity	NPD5654	Approved
0.7093	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3573	Approved
0.7079	Intermediate Similarity	NPD8264	Approved
0.7065	Intermediate Similarity	NPD7509	Discontinued
0.7065	Intermediate Similarity	NPD6931	Approved
0.7065	Intermediate Similarity	NPD6930	Phase 2
0.7065	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6314	Approved
0.7054	Intermediate Similarity	NPD6313	Approved
0.7037	Intermediate Similarity	NPD5247	Approved
0.7037	Intermediate Similarity	NPD4634	Approved
0.7037	Intermediate Similarity	NPD5135	Approved
0.7037	Intermediate Similarity	NPD5250	Approved
0.7037	Intermediate Similarity	NPD5249	Phase 3
0.7037	Intermediate Similarity	NPD5248	Approved
0.7037	Intermediate Similarity	NPD5251	Approved
0.7037	Intermediate Similarity	NPD5169	Approved
0.7037	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5362	Discontinued
0.7019	Intermediate Similarity	NPD7632	Discontinued
0.7018	Intermediate Similarity	NPD6909	Approved
0.7018	Intermediate Similarity	NPD6908	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