NPASS Compound

Structure

NPC222845 OpenBabel07101718302D 34 37 0 0 1 0 0 0 0 0999 V2000 1.5180 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9074 -1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 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 18 2 0 0 0 0 11 12 1 0 0 0 0 11 21 2 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 17 30 1 0 0 0 0 19 10 1 6 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 32 1 1 0 0 0 25 29 1 6 0 0 0 26 33 2 0 0 0 0 26 34 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:	470.34
Volume:	517.825
LogP:	5.586
LogD:	3.369
LogS:	-4.481
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	5.068
Fsp3:	0.767
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:	-5.232
MDCK Permeability:	2.609351031424012e-05
Pgp-inhibitor:	0.374
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.617

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	96.61345672607422%
Volume Distribution (VD):	0.828
Pgp-substrate:	2.9284584522247314%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.141
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.096
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	3.284
Half-life (T1/2):	0.254

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.789
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.945
Carcinogencity:	0.057
Eye Corrosion:	0.005
Eye Irritation:	0.071
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: NPC222845

Natural Product ID:	NPC222845
*Common Name:**	3Alpha,16Alpha-Dihydroxylanosta-7,9(11),24-Trien-21-Oic Acid
IUPAC Name:	(2R)-2-[(3R,5R,10S,13R,14R,16R,17R)-3,16-dihydroxy-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:
Standard InCHIKey:	XSLKAKROJKMHIT-HBZKPHNJSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-18(2)9-8-10-19(26(33)34)25-22(31)17-30(7)21-11-12-23-27(3,4)24(32)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,11,13,19,22-25,31-32H,8,10,12,14-17H2,1-7H3,(H,33,34)/t19-,22-,23+,24-,25+,28-,29-,30+/m1/s1
SMILES:	CC(=CCC[C@H]([C@H]1[C@H](O)C[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:	CHEMBL496839
PubChem CID:	16083192
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
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)91122-1]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[16933889]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27996259]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	Activity	>	125.0	ug ml-1	PMID[510321]

☑ 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 NPC222845 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	173
0.1-0.2	946
0.2-0.3	4511
0.3-0.4	13639
0.4-0.5	9072
0.5-0.6	6471
0.6-0.7	5665
0.7-0.8	1925
0.8-0.85	211
0.85-0.9	41
0.9-0.95	28
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC45324
1.0	High Similarity	NPC162001
0.967	High Similarity	NPC186810
0.967	High Similarity	NPC477813
0.967	High Similarity	NPC48647
0.9659	High Similarity	NPC23434
0.9551	High Similarity	NPC152897
0.9551	High Similarity	NPC66429
0.9551	High Similarity	NPC470376
0.9551	High Similarity	NPC470375
0.9432	High Similarity	NPC77168
0.9432	High Similarity	NPC102414
0.9432	High Similarity	NPC84271
0.9341	High Similarity	NPC263347
0.9341	High Similarity	NPC69548
0.9341	High Similarity	NPC184848
0.9326	High Similarity	NPC46281
0.9318	High Similarity	NPC247406
0.9318	High Similarity	NPC48866
0.9239	High Similarity	NPC155676
0.9231	High Similarity	NPC469406
0.9213	High Similarity	NPC54689
0.9205	High Similarity	NPC159046
0.9205	High Similarity	NPC233836
0.9205	High Similarity	NPC187376
0.9205	High Similarity	NPC312215
0.9167	High Similarity	NPC477812
0.9111	High Similarity	NPC123854
0.9101	High Similarity	NPC294480
0.9101	High Similarity	NPC242864
0.9091	High Similarity	NPC28252
0.9091	High Similarity	NPC212843
0.9091	High Similarity	NPC55309
0.9032	High Similarity	NPC173272
0.9022	High Similarity	NPC49670
0.9011	High Similarity	NPC154101
0.9011	High Similarity	NPC45269
0.9011	High Similarity	NPC297265
0.9	High Similarity	NPC474704
0.9	High Similarity	NPC475921
0.8989	High Similarity	NPC142361
0.8989	High Similarity	NPC474684
0.8925	High Similarity	NPC48330
0.8913	High Similarity	NPC243866
0.8901	High Similarity	NPC175628
0.8901	High Similarity	NPC469400
0.8901	High Similarity	NPC111585
0.8901	High Similarity	NPC148414
0.8889	High Similarity	NPC183546
0.8817	High Similarity	NPC7165
0.8804	High Similarity	NPC110657
0.8804	High Similarity	NPC212301
0.8804	High Similarity	NPC26888
0.8804	High Similarity	NPC189520
0.8804	High Similarity	NPC86266
0.8791	High Similarity	NPC474889
0.8791	High Similarity	NPC155479
0.8723	High Similarity	NPC469599
0.8723	High Similarity	NPC20546
0.871	High Similarity	NPC141497
0.871	High Similarity	NPC107674
0.871	High Similarity	NPC170220
0.871	High Similarity	NPC470224
0.8696	High Similarity	NPC471896
0.8667	High Similarity	NPC94755
0.8667	High Similarity	NPC155011
0.8646	High Similarity	NPC235464
0.8646	High Similarity	NPC166745
0.8632	High Similarity	NPC95565
0.8617	High Similarity	NPC111015
0.8617	High Similarity	NPC166906
0.8586	High Similarity	NPC472227
0.8586	High Similarity	NPC472228
0.8571	High Similarity	NPC195290
0.8571	High Similarity	NPC204450
0.8556	High Similarity	NPC474218
0.8542	High Similarity	NPC107243
0.8542	High Similarity	NPC57416
0.8542	High Similarity	NPC469432
0.8539	High Similarity	NPC69279
0.8539	High Similarity	NPC83569
0.8526	High Similarity	NPC470016
0.8526	High Similarity	NPC317586
0.8526	High Similarity	NPC127063
0.8511	High Similarity	NPC206810
0.8511	High Similarity	NPC472942
0.8511	High Similarity	NPC214697
0.8495	Intermediate Similarity	NPC273621
0.8495	Intermediate Similarity	NPC477872
0.8495	Intermediate Similarity	NPC7260
0.8495	Intermediate Similarity	NPC227467
0.8495	Intermediate Similarity	NPC120968
0.8495	Intermediate Similarity	NPC69622
0.8495	Intermediate Similarity	NPC18872
0.8495	Intermediate Similarity	NPC44240
0.8495	Intermediate Similarity	NPC290614
0.8495	Intermediate Similarity	NPC210037
0.8485	Intermediate Similarity	NPC140723
0.8485	Intermediate Similarity	NPC236390
0.8478	Intermediate Similarity	NPC471722
0.8462	Intermediate Similarity	NPC73038
0.8462	Intermediate Similarity	NPC72133
0.8454	Intermediate Similarity	NPC477854
0.8444	Intermediate Similarity	NPC165064
0.8444	Intermediate Similarity	NPC82902
0.8438	Intermediate Similarity	NPC96859
0.8438	Intermediate Similarity	NPC328162
0.8438	Intermediate Similarity	NPC305483
0.8438	Intermediate Similarity	NPC477853
0.8438	Intermediate Similarity	NPC120708
0.8427	Intermediate Similarity	NPC201852
0.8421	Intermediate Similarity	NPC80365
0.8421	Intermediate Similarity	NPC159410
0.8416	Intermediate Similarity	NPC42847
0.8416	Intermediate Similarity	NPC64844
0.8404	Intermediate Similarity	NPC212948
0.8404	Intermediate Similarity	NPC105189
0.8404	Intermediate Similarity	NPC150383
0.8404	Intermediate Similarity	NPC187722
0.8404	Intermediate Similarity	NPC301244
0.8387	Intermediate Similarity	NPC215029
0.8387	Intermediate Similarity	NPC95246
0.8387	Intermediate Similarity	NPC290972
0.8387	Intermediate Similarity	NPC474972
0.8387	Intermediate Similarity	NPC64872
0.8387	Intermediate Similarity	NPC476733
0.8387	Intermediate Similarity	NPC477943
0.8387	Intermediate Similarity	NPC474679
0.8387	Intermediate Similarity	NPC86319
0.8387	Intermediate Similarity	NPC275740
0.8387	Intermediate Similarity	NPC161751
0.8387	Intermediate Similarity	NPC25906
0.8387	Intermediate Similarity	NPC128496
0.8384	Intermediate Similarity	NPC22388
0.8384	Intermediate Similarity	NPC234892
0.8384	Intermediate Similarity	NPC293753
0.837	Intermediate Similarity	NPC167877
0.837	Intermediate Similarity	NPC96496
0.837	Intermediate Similarity	NPC477926
0.837	Intermediate Similarity	NPC317590
0.837	Intermediate Similarity	NPC136548
0.8367	Intermediate Similarity	NPC316964
0.8367	Intermediate Similarity	NPC218383
0.8367	Intermediate Similarity	NPC154072
0.8351	Intermediate Similarity	NPC320306
0.8351	Intermediate Similarity	NPC475894
0.8351	Intermediate Similarity	NPC190554
0.8351	Intermediate Similarity	NPC108078
0.8333	Intermediate Similarity	NPC312480
0.8333	Intermediate Similarity	NPC279974
0.8333	Intermediate Similarity	NPC255809
0.8333	Intermediate Similarity	NPC472485
0.8333	Intermediate Similarity	NPC88310
0.8317	Intermediate Similarity	NPC278628
0.8317	Intermediate Similarity	NPC231530
0.8316	Intermediate Similarity	NPC134826
0.8316	Intermediate Similarity	NPC475255
0.8316	Intermediate Similarity	NPC25750
0.8316	Intermediate Similarity	NPC158059
0.8316	Intermediate Similarity	NPC250575
0.8316	Intermediate Similarity	NPC477855
0.8316	Intermediate Similarity	NPC202728
0.8316	Intermediate Similarity	NPC229281
0.8316	Intermediate Similarity	NPC118519
0.8315	Intermediate Similarity	NPC38350
0.8315	Intermediate Similarity	NPC473420
0.8315	Intermediate Similarity	NPC201912
0.83	Intermediate Similarity	NPC55872
0.8298	Intermediate Similarity	NPC291028
0.8298	Intermediate Similarity	NPC171441
0.8298	Intermediate Similarity	NPC193750
0.8298	Intermediate Similarity	NPC20388
0.8298	Intermediate Similarity	NPC130278
0.8298	Intermediate Similarity	NPC191684
0.8295	Intermediate Similarity	NPC196827
0.8295	Intermediate Similarity	NPC274996
0.8283	Intermediate Similarity	NPC474327
0.8283	Intermediate Similarity	NPC99411
0.828	Intermediate Similarity	NPC328313
0.828	Intermediate Similarity	NPC182797
0.828	Intermediate Similarity	NPC131470
0.828	Intermediate Similarity	NPC470542
0.828	Intermediate Similarity	NPC44181
0.828	Intermediate Similarity	NPC474719
0.828	Intermediate Similarity	NPC471724
0.828	Intermediate Similarity	NPC143767
0.828	Intermediate Similarity	NPC52169
0.8265	Intermediate Similarity	NPC194196
0.8265	Intermediate Similarity	NPC10364
0.8265	Intermediate Similarity	NPC471717
0.8265	Intermediate Similarity	NPC197386
0.8261	Intermediate Similarity	NPC2783
0.8261	Intermediate Similarity	NPC473226
0.8261	Intermediate Similarity	NPC474970
0.8261	Intermediate Similarity	NPC6979
0.8261	Intermediate Similarity	NPC469994
0.8261	Intermediate Similarity	NPC325594
0.8261	Intermediate Similarity	NPC89077
0.8247	Intermediate Similarity	NPC471153
0.8247	Intermediate Similarity	NPC250757

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 NPC222845 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1289
0.2-0.3	3891
0.3-0.4	2601
0.4-0.5	691
0.5-0.6	199
0.6-0.7	163
0.7-0.8	154
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8602	High Similarity	NPD5281	Approved
0.8602	High Similarity	NPD5284	Approved
0.8511	High Similarity	NPD6399	Phase 3
0.8317	Intermediate Similarity	NPD6675	Approved
0.8317	Intermediate Similarity	NPD7128	Approved
0.8317	Intermediate Similarity	NPD5739	Approved
0.8317	Intermediate Similarity	NPD6402	Approved
0.8316	Intermediate Similarity	NPD4202	Approved
0.8261	Intermediate Similarity	NPD3618	Phase 1
0.8252	Intermediate Similarity	NPD6372	Approved
0.8252	Intermediate Similarity	NPD6373	Approved
0.8242	Intermediate Similarity	NPD4786	Approved
0.8191	Intermediate Similarity	NPD5328	Approved
0.8163	Intermediate Similarity	NPD4755	Approved
0.8155	Intermediate Similarity	NPD6881	Approved
0.8155	Intermediate Similarity	NPD7320	Approved
0.8155	Intermediate Similarity	NPD6899	Approved
0.8152	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6650	Approved
0.8095	Intermediate Similarity	NPD6649	Approved
0.8065	Intermediate Similarity	NPD5279	Phase 3
0.8058	Intermediate Similarity	NPD5697	Approved
0.8058	Intermediate Similarity	NPD5701	Approved
0.8043	Intermediate Similarity	NPD3133	Approved
0.8043	Intermediate Similarity	NPD3666	Approved
0.8043	Intermediate Similarity	NPD3665	Phase 1
0.8022	Intermediate Similarity	NPD3667	Approved
0.8021	Intermediate Similarity	NPD8035	Phase 2
0.8021	Intermediate Similarity	NPD7515	Phase 2
0.8021	Intermediate Similarity	NPD8034	Phase 2
0.8021	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD5286	Approved
0.8	Intermediate Similarity	NPD7290	Approved
0.8	Intermediate Similarity	NPD4700	Approved
0.8	Intermediate Similarity	NPD6883	Approved
0.8	Intermediate Similarity	NPD4696	Approved
0.8	Intermediate Similarity	NPD5285	Approved
0.7981	Intermediate Similarity	NPD6011	Approved
0.798	Intermediate Similarity	NPD6084	Phase 2
0.798	Intermediate Similarity	NPD6083	Phase 2
0.7959	Intermediate Similarity	NPD5695	Phase 3
0.7925	Intermediate Similarity	NPD8130	Phase 1
0.7925	Intermediate Similarity	NPD6617	Approved
0.7925	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6869	Approved
0.7925	Intermediate Similarity	NPD6847	Approved
0.7921	Intermediate Similarity	NPD5223	Approved
0.7905	Intermediate Similarity	NPD6014	Approved
0.7905	Intermediate Similarity	NPD6012	Approved
0.7905	Intermediate Similarity	NPD6013	Approved
0.7879	Intermediate Similarity	NPD4697	Phase 3
0.7872	Intermediate Similarity	NPD5280	Approved
0.7872	Intermediate Similarity	NPD7521	Approved
0.7872	Intermediate Similarity	NPD4694	Approved
0.7872	Intermediate Similarity	NPD7334	Approved
0.7872	Intermediate Similarity	NPD6409	Approved
0.7872	Intermediate Similarity	NPD7146	Approved
0.7872	Intermediate Similarity	NPD5330	Approved
0.7872	Intermediate Similarity	NPD6684	Approved
0.785	Intermediate Similarity	NPD6882	Approved
0.785	Intermediate Similarity	NPD8297	Approved
0.7843	Intermediate Similarity	NPD5226	Approved
0.7843	Intermediate Similarity	NPD5225	Approved
0.7843	Intermediate Similarity	NPD5211	Phase 2
0.7843	Intermediate Similarity	NPD5224	Approved
0.7843	Intermediate Similarity	NPD4633	Approved
0.7835	Intermediate Similarity	NPD6050	Approved
0.7812	Intermediate Similarity	NPD4753	Phase 2
0.7802	Intermediate Similarity	NPD7525	Registered
0.78	Intermediate Similarity	NPD7902	Approved
0.7778	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD4754	Approved
0.7767	Intermediate Similarity	NPD5175	Approved
0.7767	Intermediate Similarity	NPD5174	Approved
0.7732	Intermediate Similarity	NPD5207	Approved
0.7732	Intermediate Similarity	NPD5692	Phase 3
0.7723	Intermediate Similarity	NPD5696	Approved
0.7723	Intermediate Similarity	NPD7638	Approved
0.7708	Intermediate Similarity	NPD6903	Approved
0.7708	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5222	Approved
0.77	Intermediate Similarity	NPD5221	Approved
0.7692	Intermediate Similarity	NPD5141	Approved
0.7677	Intermediate Similarity	NPD7748	Approved
0.7667	Intermediate Similarity	NPD6116	Phase 1
0.7653	Intermediate Similarity	NPD6411	Approved
0.7653	Intermediate Similarity	NPD5694	Approved
0.7647	Intermediate Similarity	NPD7640	Approved
0.7647	Intermediate Similarity	NPD7639	Approved
0.7634	Intermediate Similarity	NPD4223	Phase 3
0.7634	Intermediate Similarity	NPD4221	Approved
0.7624	Intermediate Similarity	NPD5173	Approved
0.7619	Intermediate Similarity	NPD6008	Approved
0.7619	Intermediate Similarity	NPD4768	Approved
0.7619	Intermediate Similarity	NPD4767	Approved
0.7615	Intermediate Similarity	NPD4632	Approved
0.76	Intermediate Similarity	NPD4629	Approved
0.76	Intermediate Similarity	NPD5210	Approved
0.7579	Intermediate Similarity	NPD5329	Approved
0.7556	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6117	Approved
0.7526	Intermediate Similarity	NPD6672	Approved
0.7526	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD6098	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.7477	Intermediate Similarity	NPD4729	Approved
0.7477	Intermediate Similarity	NPD6274	Approved
0.7477	Intermediate Similarity	NPD5128	Approved
0.7477	Intermediate Similarity	NPD4730	Approved
0.7474	Intermediate Similarity	NPD3668	Phase 3
0.7474	Intermediate Similarity	NPD4197	Approved
0.7449	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6673	Approved
0.7449	Intermediate Similarity	NPD6080	Approved
0.7449	Intermediate Similarity	NPD6101	Approved
0.7449	Intermediate Similarity	NPD6904	Approved
0.7444	Intermediate Similarity	NPD7339	Approved
0.7444	Intermediate Similarity	NPD6942	Approved
0.7434	Intermediate Similarity	NPD7100	Approved
0.7434	Intermediate Similarity	NPD7101	Approved
0.7411	Intermediate Similarity	NPD6009	Approved
0.7411	Intermediate Similarity	NPD6317	Approved
0.7391	Intermediate Similarity	NPD6118	Approved
0.7391	Intermediate Similarity	NPD6115	Approved
0.7391	Intermediate Similarity	NPD6114	Approved
0.7391	Intermediate Similarity	NPD6697	Approved
0.7374	Intermediate Similarity	NPD4096	Approved
0.7368	Intermediate Similarity	NPD4788	Approved
0.7345	Intermediate Similarity	NPD6314	Approved
0.7345	Intermediate Similarity	NPD6313	Approved
0.734	Intermediate Similarity	NPD4139	Approved
0.734	Intermediate Similarity	NPD4692	Approved
0.7339	Intermediate Similarity	NPD5135	Approved
0.7339	Intermediate Similarity	NPD5247	Approved
0.7339	Intermediate Similarity	NPD5251	Approved
0.7339	Intermediate Similarity	NPD5249	Phase 3
0.7339	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD5250	Approved
0.7339	Intermediate Similarity	NPD5169	Approved
0.7339	Intermediate Similarity	NPD4634	Approved
0.7339	Intermediate Similarity	NPD5248	Approved
0.7333	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6001	Approved
0.732	Intermediate Similarity	NPD4693	Phase 3
0.732	Intermediate Similarity	NPD4138	Approved
0.732	Intermediate Similarity	NPD4689	Approved
0.732	Intermediate Similarity	NPD4690	Approved
0.732	Intermediate Similarity	NPD5205	Approved
0.732	Intermediate Similarity	NPD4688	Approved
0.7304	Intermediate Similarity	NPD6909	Approved
0.7304	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6908	Approved
0.7273	Intermediate Similarity	NPD5217	Approved
0.7273	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5215	Approved
0.7273	Intermediate Similarity	NPD5127	Approved
0.7273	Intermediate Similarity	NPD5216	Approved
0.7257	Intermediate Similarity	NPD7115	Discovery
0.7255	Intermediate Similarity	NPD5654	Approved
0.7234	Intermediate Similarity	NPD5368	Approved
0.7234	Intermediate Similarity	NPD4748	Discontinued
0.7228	Intermediate Similarity	NPD5133	Approved
0.7222	Intermediate Similarity	NPD6412	Phase 2
0.7217	Intermediate Similarity	NPD6319	Approved
0.7204	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5362	Discontinued
0.7179	Intermediate Similarity	NPD7604	Phase 2
0.7172	Intermediate Similarity	NPD5208	Approved
0.7172	Intermediate Similarity	NPD4518	Approved
0.7168	Intermediate Similarity	NPD6868	Approved
0.7158	Intermediate Similarity	NPD5369	Approved
0.7155	Intermediate Similarity	NPD5983	Phase 2
0.7143	Intermediate Similarity	NPD6926	Approved
0.7143	Intermediate Similarity	NPD6924	Approved
0.7143	Intermediate Similarity	NPD5733	Approved
0.7143	Intermediate Similarity	NPD6404	Discontinued
0.7129	Intermediate Similarity	NPD5693	Phase 1
0.7119	Intermediate Similarity	NPD7492	Approved
0.7115	Intermediate Similarity	NPD5959	Approved
0.7111	Intermediate Similarity	NPD4243	Approved
0.71	Intermediate Similarity	NPD6051	Approved
0.7083	Intermediate Similarity	NPD4270	Approved
0.7083	Intermediate Similarity	NPD6435	Approved
0.7083	Intermediate Similarity	NPD4269	Approved
0.708	Intermediate Similarity	NPD5167	Approved
0.7069	Intermediate Similarity	NPD6054	Approved
0.7069	Intermediate Similarity	NPD6059	Approved
0.7059	Intermediate Similarity	NPD5779	Approved
0.7059	Intermediate Similarity	NPD6616	Approved
0.7059	Intermediate Similarity	NPD5778	Approved
0.7059	Intermediate Similarity	NPD6336	Discontinued
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD5168	Approved
0.7	Intermediate Similarity	NPD7078	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