NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	474.3
Volume:	506.734
LogP:	4.21
LogD:	3.63
LogS:	-4.443
# Rotatable Bonds:	9
TPSA:	97.74
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.382
Synthetic Accessibility Score:	4.799
Fsp3:	0.786
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:	-5.406
MDCK Permeability:	2.559029780968558e-05
Pgp-inhibitor:	0.217
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.443

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.62
Plasma Protein Binding (PPB):	67.4758529663086%
Volume Distribution (VD):	0.322
Pgp-substrate:	29.37639045715332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.304
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.282
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	13.78
Half-life (T1/2):	0.566

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.405
Drug-inuced Liver Injury (DILI):	0.227
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.296
Skin Sensitization:	0.05
Carcinogencity:	0.152
Eye Corrosion:	0.838
Eye Irritation:	0.022
Respiratory Toxicity:	0.49

Download Data

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

Natural Product: NPC477147

Natural Product ID:	NPC477147
*Common Name:**	(4R)-4-[(3R,3aR,6S,7S,9S,9bR)-9-hydroxy-6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-5-oxo-7-prop-1-en-2-yl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[a]naphthalen-3-yl]pentanoic acid
IUPAC Name:	(4R)-4-[(3R,3aR,6S,7S,9S,9bR)-9-hydroxy-6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-5-oxo-7-prop-1-en-2-yl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[a]naphthalen-3-yl]pentanoic acid
Synonyms:
Standard InCHIKey:	NIMMHBASIZOWOI-IDISLCOVSA-N
Standard InCHI:	InChI=1S/C28H42O6/c1-16(2)19-14-20(29)25-24(26(19,4)12-11-23(33)34-7)21(30)15-28(6)18(10-13-27(25,28)5)17(3)8-9-22(31)32/h17-20,29H,1,8-15H2,2-7H3,(H,31,32)/t17-,18-,19+,20+,26+,27+,28-/m1/s1
SMILES:	C[C@H](CCC(=O)O)[C@H]1CC[C@@]2([C@@]1(CC(=O)C3=C2[C@H](C[C@H]([C@]3(C)CCC(=O)OC)C(=C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90670060
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO33519	Ganoderma cochlear	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[24559087]

☑ 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
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	21.01	U/L	PMID[24559087]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	19.32	U/L	PMID[24559087]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	19.73	U/L	PMID[24559087]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	28.23	U/L	PMID[24559087]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	26.54	U/L	PMID[24559087]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	26.19	U/L	PMID[24559087]

☑ 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 NPC477147 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	1035
0.2-0.3	4913
0.3-0.4	13529
0.4-0.5	9619
0.5-0.6	6333
0.6-0.7	5380
0.7-0.8	1525
0.8-0.85	168
0.85-0.9	31
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477149
0.9881	High Similarity	NPC214387
0.9438	High Similarity	NPC328371
0.9326	High Similarity	NPC174948
0.9326	High Similarity	NPC318282
0.9326	High Similarity	NPC469995
0.9326	High Similarity	NPC173875
0.9222	High Similarity	NPC472941
0.9222	High Similarity	NPC456
0.9213	High Similarity	NPC184870
0.9121	High Similarity	NPC320306
0.9011	High Similarity	NPC7124
0.9011	High Similarity	NPC3772
0.8936	High Similarity	NPC308726
0.8936	High Similarity	NPC119601
0.8925	High Similarity	NPC327431
0.8925	High Similarity	NPC51370
0.8925	High Similarity	NPC287833
0.8913	High Similarity	NPC121339
0.8913	High Similarity	NPC18319
0.8913	High Similarity	NPC106557
0.8901	High Similarity	NPC470016
0.8901	High Similarity	NPC37646
0.8901	High Similarity	NPC317586
0.8889	High Similarity	NPC470254
0.8889	High Similarity	NPC472930
0.8876	High Similarity	NPC469400
0.8851	High Similarity	NPC322159
0.8842	High Similarity	NPC236390
0.8837	High Similarity	NPC165064
0.883	High Similarity	NPC302537
0.883	High Similarity	NPC163372
0.883	High Similarity	NPC472924
0.8817	High Similarity	NPC197386
0.8817	High Similarity	NPC235464
0.8817	High Similarity	NPC166745
0.8817	High Similarity	NPC471717
0.8804	High Similarity	NPC40765
0.8804	High Similarity	NPC243525
0.8791	High Similarity	NPC166906
0.8791	High Similarity	NPC469406
0.8778	High Similarity	NPC233116
0.8778	High Similarity	NPC107690
0.8778	High Similarity	NPC63748
0.8764	High Similarity	NPC155479
0.8764	High Similarity	NPC310236
0.8764	High Similarity	NPC123912
0.8737	High Similarity	NPC204450
0.8737	High Similarity	NPC234892
0.8737	High Similarity	NPC293753
0.8737	High Similarity	NPC195290
0.8736	High Similarity	NPC474083
0.8723	High Similarity	NPC299971
0.8723	High Similarity	NPC205899
0.8723	High Similarity	NPC144660
0.8723	High Similarity	NPC307954
0.8723	High Similarity	NPC476274
0.871	High Similarity	NPC253826
0.871	High Similarity	NPC122294
0.8696	High Similarity	NPC476174
0.8681	High Similarity	NPC243866
0.8681	High Similarity	NPC69454
0.8667	High Similarity	NPC48010
0.8652	High Similarity	NPC249889
0.8652	High Similarity	NPC183546
0.8652	High Similarity	NPC294480
0.8652	High Similarity	NPC193843
0.8652	High Similarity	NPC242864
0.8636	High Similarity	NPC28252
0.8636	High Similarity	NPC55309
0.8636	High Similarity	NPC212843
0.8636	High Similarity	NPC72133
0.8632	High Similarity	NPC224720
0.8632	High Similarity	NPC476223
0.8632	High Similarity	NPC99411
0.8632	High Similarity	NPC476240
0.8621	High Similarity	NPC164577
0.8621	High Similarity	NPC473246
0.8617	High Similarity	NPC16021
0.8617	High Similarity	NPC10364
0.8602	High Similarity	NPC96859
0.8602	High Similarity	NPC328162
0.8602	High Similarity	NPC301534
0.8602	High Similarity	NPC305483
0.8602	High Similarity	NPC249954
0.8602	High Similarity	NPC250757
0.8571	High Similarity	NPC473998
0.8571	High Similarity	NPC297265
0.8556	High Similarity	NPC309603
0.8556	High Similarity	NPC473999
0.8556	High Similarity	NPC474889
0.8556	High Similarity	NPC54689
0.8542	High Similarity	NPC56498
0.8542	High Similarity	NPC281702
0.8539	High Similarity	NPC136948
0.8539	High Similarity	NPC187376
0.8539	High Similarity	NPC312215
0.8539	High Similarity	NPC159046
0.8539	High Similarity	NPC233836
0.8526	High Similarity	NPC241221
0.8526	High Similarity	NPC266955
0.8523	High Similarity	NPC471224
0.8511	High Similarity	NPC475894
0.8511	High Similarity	NPC107243
0.8506	High Similarity	NPC97913
0.8506	High Similarity	NPC168188
0.8506	High Similarity	NPC470015
0.8495	Intermediate Similarity	NPC472932
0.8495	Intermediate Similarity	NPC259286
0.8488	Intermediate Similarity	NPC477372
0.8478	Intermediate Similarity	NPC214697
0.8469	Intermediate Similarity	NPC323834
0.8462	Intermediate Similarity	NPC111585
0.8462	Intermediate Similarity	NPC148414
0.8462	Intermediate Similarity	NPC175628
0.8444	Intermediate Similarity	NPC143767
0.8444	Intermediate Similarity	NPC131470
0.8444	Intermediate Similarity	NPC471722
0.8444	Intermediate Similarity	NPC472870
0.8438	Intermediate Similarity	NPC115899
0.8421	Intermediate Similarity	NPC48647
0.8421	Intermediate Similarity	NPC478056
0.8421	Intermediate Similarity	NPC108368
0.8421	Intermediate Similarity	NPC57079
0.8409	Intermediate Similarity	NPC85774
0.8409	Intermediate Similarity	NPC214043
0.8409	Intermediate Similarity	NPC472865
0.8404	Intermediate Similarity	NPC155676
0.8404	Intermediate Similarity	NPC29152
0.8391	Intermediate Similarity	NPC327969
0.8391	Intermediate Similarity	NPC321289
0.8387	Intermediate Similarity	NPC7165
0.8387	Intermediate Similarity	NPC53685
0.8387	Intermediate Similarity	NPC8993
0.8384	Intermediate Similarity	NPC472925
0.8384	Intermediate Similarity	NPC91034
0.8372	Intermediate Similarity	NPC271104
0.837	Intermediate Similarity	NPC26888
0.837	Intermediate Similarity	NPC154101
0.837	Intermediate Similarity	NPC474018
0.837	Intermediate Similarity	NPC473986
0.837	Intermediate Similarity	NPC475806
0.837	Intermediate Similarity	NPC23434
0.837	Intermediate Similarity	NPC212948
0.837	Intermediate Similarity	NPC470113
0.837	Intermediate Similarity	NPC45269
0.837	Intermediate Similarity	NPC476187
0.837	Intermediate Similarity	NPC204341
0.8367	Intermediate Similarity	NPC28656
0.8352	Intermediate Similarity	NPC84271
0.8352	Intermediate Similarity	NPC102414
0.8352	Intermediate Similarity	NPC262858
0.8352	Intermediate Similarity	NPC146554
0.8352	Intermediate Similarity	NPC475921
0.8352	Intermediate Similarity	NPC86319
0.8352	Intermediate Similarity	NPC474704
0.8352	Intermediate Similarity	NPC275740
0.8352	Intermediate Similarity	NPC31985
0.8352	Intermediate Similarity	NPC5509
0.8352	Intermediate Similarity	NPC262043
0.8352	Intermediate Similarity	NPC77168
0.8352	Intermediate Similarity	NPC472240
0.8352	Intermediate Similarity	NPC1015
0.8352	Intermediate Similarity	NPC66344
0.8351	Intermediate Similarity	NPC136289
0.8333	Intermediate Similarity	NPC316964
0.8333	Intermediate Similarity	NPC477521
0.8333	Intermediate Similarity	NPC287079
0.8333	Intermediate Similarity	NPC142361
0.8333	Intermediate Similarity	NPC128644
0.8333	Intermediate Similarity	NPC474684
0.8333	Intermediate Similarity	NPC167877
0.8333	Intermediate Similarity	NPC96496
0.8333	Intermediate Similarity	NPC312561
0.8333	Intermediate Similarity	NPC475740
0.8316	Intermediate Similarity	NPC156546
0.8316	Intermediate Similarity	NPC53844
0.8316	Intermediate Similarity	NPC43747
0.8316	Intermediate Similarity	NPC57416
0.8316	Intermediate Similarity	NPC108078
0.8316	Intermediate Similarity	NPC141401
0.8315	Intermediate Similarity	NPC94531
0.8315	Intermediate Similarity	NPC283733
0.8315	Intermediate Similarity	NPC123319
0.8315	Intermediate Similarity	NPC311702
0.83	Intermediate Similarity	NPC295244
0.8298	Intermediate Similarity	NPC69548
0.8298	Intermediate Similarity	NPC271195
0.8298	Intermediate Similarity	NPC255809
0.8298	Intermediate Similarity	NPC184848
0.8298	Intermediate Similarity	NPC297199
0.8295	Intermediate Similarity	NPC310470
0.8295	Intermediate Similarity	NPC49019
0.828	Intermediate Similarity	NPC107674
0.828	Intermediate Similarity	NPC472942
0.828	Intermediate Similarity	NPC472871
0.828	Intermediate Similarity	NPC474736
0.828	Intermediate Similarity	NPC38232
0.828	Intermediate Similarity	NPC66429
0.828	Intermediate Similarity	NPC206810

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 NPC477147 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1591
0.2-0.3	3859
0.3-0.4	2395
0.4-0.5	669
0.5-0.6	203
0.6-0.7	208
0.7-0.8	76
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8152	Intermediate Similarity	NPD5328	Approved
0.814	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6083	Phase 2
0.8125	Intermediate Similarity	NPD6084	Phase 2
0.8105	Intermediate Similarity	NPD5695	Phase 3
0.8085	Intermediate Similarity	NPD6399	Phase 3
0.8043	Intermediate Similarity	NPD6672	Approved
0.8043	Intermediate Similarity	NPD5737	Approved
0.8022	Intermediate Similarity	NPD6684	Approved
0.8022	Intermediate Similarity	NPD5279	Phase 3
0.8022	Intermediate Similarity	NPD7334	Approved
0.8022	Intermediate Similarity	NPD7146	Approved
0.8022	Intermediate Similarity	NPD3618	Phase 1
0.8022	Intermediate Similarity	NPD7521	Approved
0.8022	Intermediate Similarity	NPD6409	Approved
0.8022	Intermediate Similarity	NPD5330	Approved
0.8	Intermediate Similarity	NPD3665	Phase 1
0.8	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD3666	Approved
0.8	Intermediate Similarity	NPD3133	Approved
0.7979	Intermediate Similarity	NPD6079	Approved
0.7979	Intermediate Similarity	NPD7515	Phase 2
0.7959	Intermediate Similarity	NPD7640	Approved
0.7959	Intermediate Similarity	NPD7639	Approved
0.7921	Intermediate Similarity	NPD5739	Approved
0.7921	Intermediate Similarity	NPD7128	Approved
0.7921	Intermediate Similarity	NPD6675	Approved
0.7921	Intermediate Similarity	NPD6402	Approved
0.7857	Intermediate Similarity	NPD7638	Approved
0.7849	Intermediate Similarity	NPD6903	Approved
0.7849	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7748	Approved
0.7789	Intermediate Similarity	NPD5284	Approved
0.7789	Intermediate Similarity	NPD5281	Approved
0.7778	Intermediate Similarity	NPD3667	Approved
0.7767	Intermediate Similarity	NPD6899	Approved
0.7767	Intermediate Similarity	NPD7320	Approved
0.7767	Intermediate Similarity	NPD6881	Approved
0.7766	Intermediate Similarity	NPD4753	Phase 2
0.7717	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4202	Approved
0.7692	Intermediate Similarity	NPD6372	Approved
0.7692	Intermediate Similarity	NPD5362	Discontinued
0.7692	Intermediate Similarity	NPD6373	Approved
0.7685	Intermediate Similarity	NPD7115	Discovery
0.7684	Intermediate Similarity	NPD5785	Approved
0.7677	Intermediate Similarity	NPD5696	Approved
0.767	Intermediate Similarity	NPD5697	Approved
0.767	Intermediate Similarity	NPD5701	Approved
0.7653	Intermediate Similarity	NPD5221	Approved
0.7653	Intermediate Similarity	NPD5222	Approved
0.7653	Intermediate Similarity	NPD4697	Phase 3
0.7653	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5211	Phase 2
0.7619	Intermediate Similarity	NPD6883	Approved
0.7619	Intermediate Similarity	NPD7290	Approved
0.7619	Intermediate Similarity	NPD7102	Approved
0.7604	Intermediate Similarity	NPD6050	Approved
0.7596	Intermediate Similarity	NPD6011	Approved
0.7582	Intermediate Similarity	NPD4223	Phase 3
0.7582	Intermediate Similarity	NPD4221	Approved
0.7579	Intermediate Similarity	NPD6080	Approved
0.7579	Intermediate Similarity	NPD6673	Approved
0.7579	Intermediate Similarity	NPD6904	Approved
0.7576	Intermediate Similarity	NPD4755	Approved
0.7576	Intermediate Similarity	NPD7902	Approved
0.7576	Intermediate Similarity	NPD5173	Approved
0.7551	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6617	Approved
0.7547	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6650	Approved
0.7547	Intermediate Similarity	NPD6869	Approved
0.7547	Intermediate Similarity	NPD6649	Approved
0.7547	Intermediate Similarity	NPD6847	Approved
0.7547	Intermediate Similarity	NPD8130	Phase 1
0.7527	Intermediate Similarity	NPD5329	Approved
0.7527	Intermediate Similarity	NPD5363	Approved
0.7524	Intermediate Similarity	NPD6013	Approved
0.7524	Intermediate Similarity	NPD6014	Approved
0.7524	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD5692	Phase 3
0.7477	Intermediate Similarity	NPD6882	Approved
0.7477	Intermediate Similarity	NPD8297	Approved
0.7476	Intermediate Similarity	NPD5141	Approved
0.7451	Intermediate Similarity	NPD7632	Discontinued
0.7447	Intermediate Similarity	NPD5280	Approved
0.7447	Intermediate Similarity	NPD4694	Approved
0.7447	Intermediate Similarity	NPD5690	Phase 2
0.7426	Intermediate Similarity	NPD4700	Approved
0.7426	Intermediate Similarity	NPD4696	Approved
0.7426	Intermediate Similarity	NPD5285	Approved
0.7426	Intermediate Similarity	NPD6404	Discontinued
0.7426	Intermediate Similarity	NPD5286	Approved
0.7423	Intermediate Similarity	NPD5693	Phase 1
0.7423	Intermediate Similarity	NPD8035	Phase 2
0.7423	Intermediate Similarity	NPD5694	Approved
0.7423	Intermediate Similarity	NPD8034	Phase 2
0.7419	Intermediate Similarity	NPD4197	Approved
0.7391	Intermediate Similarity	NPD4269	Approved
0.7391	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4270	Approved
0.7374	Intermediate Similarity	NPD4629	Approved
0.7374	Intermediate Similarity	NPD5210	Approved
0.7353	Intermediate Similarity	NPD5223	Approved
0.7347	Intermediate Similarity	NPD5778	Approved
0.7347	Intermediate Similarity	NPD5779	Approved
0.734	Intermediate Similarity	NPD1694	Approved
0.7333	Intermediate Similarity	NPD3617	Approved
0.732	Intermediate Similarity	NPD5207	Approved
0.7312	Intermediate Similarity	NPD4788	Approved
0.7292	Intermediate Similarity	NPD5208	Approved
0.7282	Intermediate Similarity	NPD5225	Approved
0.7282	Intermediate Similarity	NPD4633	Approved
0.7282	Intermediate Similarity	NPD5224	Approved
0.7282	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD7900	Approved
0.7273	Intermediate Similarity	NPD6868	Approved
0.7273	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5205	Approved
0.7263	Intermediate Similarity	NPD4689	Approved
0.7263	Intermediate Similarity	NPD4688	Approved
0.7263	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6098	Approved
0.7263	Intermediate Similarity	NPD4623	Approved
0.7263	Intermediate Similarity	NPD5786	Approved
0.7263	Intermediate Similarity	NPD4138	Approved
0.7263	Intermediate Similarity	NPD4693	Phase 3
0.7263	Intermediate Similarity	NPD4690	Approved
0.7263	Intermediate Similarity	NPD4519	Discontinued
0.7248	Intermediate Similarity	NPD4632	Approved
0.7245	Intermediate Similarity	NPD6411	Approved
0.7245	Intermediate Similarity	NPD7637	Suspended
0.7234	Intermediate Similarity	NPD3668	Phase 3
0.7216	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4754	Approved
0.7212	Intermediate Similarity	NPD5175	Approved
0.7212	Intermediate Similarity	NPD5174	Approved
0.7174	Intermediate Similarity	NPD4252	Approved
0.717	Intermediate Similarity	NPD6412	Phase 2
0.7157	Intermediate Similarity	NPD4225	Approved
0.7156	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD6335	Approved
0.7128	Intermediate Similarity	NPD7154	Phase 3
0.7128	Intermediate Similarity	NPD5332	Approved
0.7128	Intermediate Similarity	NPD5331	Approved
0.7117	Intermediate Similarity	NPD6274	Approved
0.7111	Intermediate Similarity	NPD6117	Approved
0.71	Intermediate Similarity	NPD6001	Approved
0.7097	Intermediate Similarity	NPD4790	Discontinued
0.7097	Intermediate Similarity	NPD5369	Approved
0.7097	Intermediate Similarity	NPD4692	Approved
0.7097	Intermediate Similarity	NPD4139	Approved
0.708	Intermediate Similarity	NPD7101	Approved
0.708	Intermediate Similarity	NPD7100	Approved
0.7079	Intermediate Similarity	NPD5733	Approved
0.7075	Intermediate Similarity	NPD4767	Approved
0.7075	Intermediate Similarity	NPD4768	Approved
0.7075	Intermediate Similarity	NPD6008	Approved
0.7054	Intermediate Similarity	NPD6317	Approved
0.7054	Intermediate Similarity	NPD6009	Approved
0.7041	Intermediate Similarity	NPD6051	Approved
0.7041	Intermediate Similarity	NPD6101	Approved
0.7041	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6116	Phase 1
0.703	Intermediate Similarity	NPD5654	Approved
0.7021	Intermediate Similarity	NPD6435	Approved
0.7	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD7339	Approved
0.6991	Remote Similarity	NPD6314	Approved
0.6991	Remote Similarity	NPD6313	Approved
0.6989	Remote Similarity	NPD4819	Approved
0.6989	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5368	Approved
0.6989	Remote Similarity	NPD4695	Discontinued
0.6989	Remote Similarity	NPD4820	Approved
0.6989	Remote Similarity	NPD7525	Registered
0.6989	Remote Similarity	NPD4821	Approved
0.6989	Remote Similarity	NPD4822	Approved
0.697	Remote Similarity	NPD4096	Approved
0.6957	Remote Similarity	NPD6697	Approved
0.6957	Remote Similarity	NPD6118	Approved
0.6957	Remote Similarity	NPD4268	Approved
0.6957	Remote Similarity	NPD4271	Approved
0.6957	Remote Similarity	NPD6114	Approved
0.6957	Remote Similarity	NPD6115	Approved
0.6957	Remote Similarity	NPD6908	Approved
0.6957	Remote Similarity	NPD6909	Approved
0.6944	Remote Similarity	NPD5128	Approved
0.6944	Remote Similarity	NPD6686	Approved
0.6944	Remote Similarity	NPD4730	Approved
0.6944	Remote Similarity	NPD4729	Approved
0.6944	Remote Similarity	NPD5168	Approved
0.6939	Remote Similarity	NPD4518	Approved
0.6932	Remote Similarity	NPD4747	Approved
0.6893	Remote Similarity	NPD5959	Approved
0.6889	Remote Similarity	NPD4687	Approved
0.6889	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4195	Approved
0.6881	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6400	Clinical (unspecified phase)

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