NPASS Compound

Structure

CID73882 OpenBabel06191715412D 23 25 0 0 1 0 0 0 0 0999 V2000 -1.2247 -1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 0.6088 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 4.8301 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 2 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 5.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 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 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 5 18 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 14 19 1 0 0 0 0 15 19 1 6 0 0 0 15 20 1 0 0 0 0 16 18 1 1 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	2.976
LogD:	2.345
LogS:	-3.009
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	4.631
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.292
MDCK Permeability:	1.4573015505447984e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.641
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	92.72145080566406%
Volume Distribution (VD):	0.517
Pgp-substrate:	7.15178108215332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.338
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.22
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.46
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	1.586
Half-life (T1/2):	0.353

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.312
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.364
Maximum Recommended Daily Dose:	0.307
Skin Sensitization:	0.242
Carcinogencity:	0.616
Eye Corrosion:	0.055
Eye Irritation:	0.106
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC73882

Natural Product ID:	NPC73882
*Common Name:**	12Alpha-Hydroxy-8,15-Isopimaradien-18-Oic Acid
IUPAC Name:	(1R,4aS,6S,7S,10aR)-7-ethenyl-6-hydroxy-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	YMYLSONMRJEVBJ-QQXMDYFESA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-5-18(2)12-13-7-8-15-19(3,14(13)11-16(18)21)9-6-10-20(15,4)17(22)23/h5,15-16,21H,1,6-12H2,2-4H3,(H,22,23)/t15-,16+,18-,19-,20-/m1/s1
SMILES:	C=C[C@]1(C)CC2=C(C[C@@H]1O)[C@@]1(C)CCC[C@](C)([C@@H]1CC2)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689207
PubChem CID:	51040469
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
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[500922]

☑ 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 NPC73882 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	166
0.1-0.2	1017
0.2-0.3	4814
0.3-0.4	14870
0.4-0.5	8755
0.5-0.6	6801
0.6-0.7	4395
0.7-0.8	1733
0.8-0.85	120
0.85-0.9	25
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC473420
0.9024	High Similarity	NPC82979
0.8941	High Similarity	NPC301244
0.8916	High Similarity	NPC71507
0.8916	High Similarity	NPC233836
0.8916	High Similarity	NPC187376
0.8916	High Similarity	NPC159046
0.881	High Similarity	NPC242864
0.881	High Similarity	NPC473242
0.881	High Similarity	NPC181225
0.881	High Similarity	NPC290690
0.881	High Similarity	NPC470629
0.881	High Similarity	NPC474512
0.881	High Similarity	NPC17733
0.8795	High Similarity	NPC155011
0.8795	High Similarity	NPC55309
0.8795	High Similarity	NPC28252
0.8795	High Similarity	NPC56588
0.8795	High Similarity	NPC325594
0.8795	High Similarity	NPC73038
0.8795	High Similarity	NPC473226
0.8795	High Similarity	NPC72638
0.878	High Similarity	NPC171789
0.8736	High Similarity	NPC80365
0.8718	High Similarity	NPC69143
0.8706	High Similarity	NPC143232
0.8706	High Similarity	NPC470588
0.8706	High Similarity	NPC77168
0.8706	High Similarity	NPC84271
0.8706	High Similarity	NPC102414
0.8706	High Similarity	NPC198664
0.8706	High Similarity	NPC274330
0.869	High Similarity	NPC130577
0.869	High Similarity	NPC142361
0.869	High Similarity	NPC51700
0.869	High Similarity	NPC88716
0.869	High Similarity	NPC474684
0.869	High Similarity	NPC102683
0.869	High Similarity	NPC68160
0.869	High Similarity	NPC142415
0.869	High Similarity	NPC293564
0.869	High Similarity	NPC477926
0.869	High Similarity	NPC18064
0.869	High Similarity	NPC171203
0.869	High Similarity	NPC307426
0.869	High Similarity	NPC98442
0.869	High Similarity	NPC242468
0.8659	High Similarity	NPC312480
0.8642	High Similarity	NPC14151
0.8621	High Similarity	NPC133579
0.8621	High Similarity	NPC474806
0.8605	High Similarity	NPC126369
0.8605	High Similarity	NPC111110
0.8605	High Similarity	NPC470589
0.859	High Similarity	NPC279666
0.859	High Similarity	NPC192540
0.8588	High Similarity	NPC246708
0.8588	High Similarity	NPC182797
0.8588	High Similarity	NPC52169
0.8588	High Similarity	NPC473229
0.8588	High Similarity	NPC40552
0.8571	High Similarity	NPC6979
0.8537	High Similarity	NPC151519
0.8506	High Similarity	NPC187722
0.8506	High Similarity	NPC297265
0.8506	High Similarity	NPC26888
0.8488	Intermediate Similarity	NPC225585
0.8488	Intermediate Similarity	NPC293048
0.8488	Intermediate Similarity	NPC128496
0.8488	Intermediate Similarity	NPC25906
0.8488	Intermediate Similarity	NPC64872
0.8488	Intermediate Similarity	NPC270768
0.8488	Intermediate Similarity	NPC127689
0.8488	Intermediate Similarity	NPC121798
0.8488	Intermediate Similarity	NPC59263
0.8488	Intermediate Similarity	NPC234346
0.8488	Intermediate Similarity	NPC161751
0.8488	Intermediate Similarity	NPC130520
0.8488	Intermediate Similarity	NPC475921
0.8488	Intermediate Similarity	NPC263393
0.8488	Intermediate Similarity	NPC474686
0.8488	Intermediate Similarity	NPC290972
0.8488	Intermediate Similarity	NPC474704
0.8488	Intermediate Similarity	NPC474972
0.8488	Intermediate Similarity	NPC61543
0.8488	Intermediate Similarity	NPC95246
0.8481	Intermediate Similarity	NPC309399
0.8462	Intermediate Similarity	NPC283908
0.8462	Intermediate Similarity	NPC241854
0.8462	Intermediate Similarity	NPC161923
0.8462	Intermediate Similarity	NPC476046
0.8462	Intermediate Similarity	NPC103958
0.8462	Intermediate Similarity	NPC251970
0.8462	Intermediate Similarity	NPC183503
0.8444	Intermediate Similarity	NPC21728
0.8434	Intermediate Similarity	NPC470948
0.8427	Intermediate Similarity	NPC32118
0.8415	Intermediate Similarity	NPC142163
0.8409	Intermediate Similarity	NPC118519
0.8409	Intermediate Similarity	NPC202728
0.8409	Intermediate Similarity	NPC158059
0.8409	Intermediate Similarity	NPC229281
0.8395	Intermediate Similarity	NPC474113
0.8395	Intermediate Similarity	NPC100906
0.8391	Intermediate Similarity	NPC291028
0.8391	Intermediate Similarity	NPC46441
0.8391	Intermediate Similarity	NPC290614
0.8391	Intermediate Similarity	NPC86372
0.8391	Intermediate Similarity	NPC210037
0.8391	Intermediate Similarity	NPC477872
0.8391	Intermediate Similarity	NPC474728
0.8391	Intermediate Similarity	NPC111585
0.8391	Intermediate Similarity	NPC172361
0.8391	Intermediate Similarity	NPC7260
0.8391	Intermediate Similarity	NPC18872
0.8391	Intermediate Similarity	NPC120968
0.8391	Intermediate Similarity	NPC273621
0.8391	Intermediate Similarity	NPC148414
0.8391	Intermediate Similarity	NPC469400
0.8391	Intermediate Similarity	NPC175628
0.8391	Intermediate Similarity	NPC130278
0.8391	Intermediate Similarity	NPC227467
0.8391	Intermediate Similarity	NPC49320
0.8372	Intermediate Similarity	NPC471722
0.8353	Intermediate Similarity	NPC94666
0.8353	Intermediate Similarity	NPC475022
0.8353	Intermediate Similarity	NPC222613
0.8353	Intermediate Similarity	NPC118648
0.8353	Intermediate Similarity	NPC94755
0.8333	Intermediate Similarity	NPC221758
0.8333	Intermediate Similarity	NPC165064
0.8333	Intermediate Similarity	NPC9487
0.8333	Intermediate Similarity	NPC88847
0.8333	Intermediate Similarity	NPC173272
0.8333	Intermediate Similarity	NPC180834
0.8333	Intermediate Similarity	NPC59453
0.8315	Intermediate Similarity	NPC166906
0.8315	Intermediate Similarity	NPC159365
0.8315	Intermediate Similarity	NPC6818
0.8315	Intermediate Similarity	NPC209868
0.8315	Intermediate Similarity	NPC469406
0.8315	Intermediate Similarity	NPC87095
0.8315	Intermediate Similarity	NPC114159
0.8315	Intermediate Similarity	NPC191412
0.8313	Intermediate Similarity	NPC48362
0.8313	Intermediate Similarity	NPC260956
0.8295	Intermediate Similarity	NPC84319
0.8295	Intermediate Similarity	NPC285184
0.8295	Intermediate Similarity	NPC145067
0.8295	Intermediate Similarity	NPC288833
0.8295	Intermediate Similarity	NPC212301
0.8295	Intermediate Similarity	NPC52021
0.8295	Intermediate Similarity	NPC324341
0.8295	Intermediate Similarity	NPC71074
0.8295	Intermediate Similarity	NPC228784
0.8295	Intermediate Similarity	NPC282616
0.8295	Intermediate Similarity	NPC189520
0.8295	Intermediate Similarity	NPC474525
0.8295	Intermediate Similarity	NPC966
0.8295	Intermediate Similarity	NPC470590
0.8295	Intermediate Similarity	NPC472149
0.8295	Intermediate Similarity	NPC86266
0.8295	Intermediate Similarity	NPC158030
0.8295	Intermediate Similarity	NPC65120
0.8295	Intermediate Similarity	NPC23434
0.8295	Intermediate Similarity	NPC38754
0.8295	Intermediate Similarity	NPC77099
0.8295	Intermediate Similarity	NPC110657
0.8295	Intermediate Similarity	NPC235884
0.8295	Intermediate Similarity	NPC300351
0.8295	Intermediate Similarity	NPC306541
0.8295	Intermediate Similarity	NPC60755
0.8295	Intermediate Similarity	NPC475708
0.8295	Intermediate Similarity	NPC155120
0.8295	Intermediate Similarity	NPC477574
0.8295	Intermediate Similarity	NPC235704
0.8295	Intermediate Similarity	NPC4036
0.8295	Intermediate Similarity	NPC25299
0.8295	Intermediate Similarity	NPC233455
0.8295	Intermediate Similarity	NPC105189
0.8293	Intermediate Similarity	NPC2482
0.8293	Intermediate Similarity	NPC26139
0.8276	Intermediate Similarity	NPC474889
0.8276	Intermediate Similarity	NPC30522
0.8272	Intermediate Similarity	NPC179028
0.8272	Intermediate Similarity	NPC247783
0.8272	Intermediate Similarity	NPC321514
0.8272	Intermediate Similarity	NPC269543
0.8256	Intermediate Similarity	NPC298904
0.8256	Intermediate Similarity	NPC73064
0.8256	Intermediate Similarity	NPC58063
0.8242	Intermediate Similarity	NPC108078
0.8235	Intermediate Similarity	NPC133954
0.8228	Intermediate Similarity	NPC301065
0.8222	Intermediate Similarity	NPC48330
0.8222	Intermediate Similarity	NPC470016
0.8222	Intermediate Similarity	NPC96916
0.8222	Intermediate Similarity	NPC162001
0.8222	Intermediate Similarity	NPC222845
0.8222	Intermediate Similarity	NPC53565

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 NPC73882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1470
0.2-0.3	3791
0.3-0.4	2485
0.4-0.5	715
0.5-0.6	258
0.6-0.7	239
0.7-0.8	39
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8537	High Similarity	NPD3667	Approved
0.8333	Intermediate Similarity	NPD4786	Approved
0.8295	Intermediate Similarity	NPD7515	Phase 2
0.814	Intermediate Similarity	NPD3618	Phase 1
0.809	Intermediate Similarity	NPD6411	Approved
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7912	Intermediate Similarity	NPD7748	Approved
0.7907	Intermediate Similarity	NPD3666	Approved
0.7907	Intermediate Similarity	NPD3133	Approved
0.7907	Intermediate Similarity	NPD3665	Phase 1
0.7889	Intermediate Similarity	NPD6079	Approved
0.7865	Intermediate Similarity	NPD5328	Approved
0.7865	Intermediate Similarity	NPD6101	Approved
0.7865	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5279	Phase 3
0.7701	Intermediate Similarity	NPD3668	Phase 3
0.7667	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7902	Approved
0.7609	Intermediate Similarity	NPD4202	Approved
0.759	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5222	Approved
0.7553	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5221	Approved
0.7528	Intermediate Similarity	NPD6684	Approved
0.7528	Intermediate Similarity	NPD7334	Approved
0.7528	Intermediate Similarity	NPD5330	Approved
0.7528	Intermediate Similarity	NPD7521	Approved
0.7528	Intermediate Similarity	NPD6409	Approved
0.7528	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD5284	Approved
0.7474	Intermediate Similarity	NPD5173	Approved
0.747	Intermediate Similarity	NPD6942	Approved
0.747	Intermediate Similarity	NPD7339	Approved
0.7447	Intermediate Similarity	NPD5695	Phase 3
0.7444	Intermediate Similarity	NPD3573	Approved
0.7442	Intermediate Similarity	NPD4695	Discontinued
0.7419	Intermediate Similarity	NPD5778	Approved
0.7419	Intermediate Similarity	NPD5779	Approved
0.74	Intermediate Similarity	NPD5697	Approved
0.7368	Intermediate Similarity	NPD4697	Phase 3
0.7363	Intermediate Similarity	NPD6903	Approved
0.7363	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7900	Approved
0.7333	Intermediate Similarity	NPD5690	Phase 2
0.7327	Intermediate Similarity	NPD6011	Approved
0.7327	Intermediate Similarity	NPD6899	Approved
0.7327	Intermediate Similarity	NPD6881	Approved
0.7326	Intermediate Similarity	NPD7645	Phase 2
0.732	Intermediate Similarity	NPD5285	Approved
0.732	Intermediate Similarity	NPD5286	Approved
0.732	Intermediate Similarity	NPD4696	Approved
0.73	Intermediate Similarity	NPD6675	Approved
0.73	Intermediate Similarity	NPD5739	Approved
0.73	Intermediate Similarity	NPD7128	Approved
0.73	Intermediate Similarity	NPD6402	Approved
0.7292	Intermediate Similarity	NPD6083	Phase 2
0.7292	Intermediate Similarity	NPD6084	Phase 2
0.7292	Intermediate Similarity	NPD4755	Approved
0.7283	Intermediate Similarity	NPD4753	Phase 2
0.7273	Intermediate Similarity	NPD4221	Approved
0.7273	Intermediate Similarity	NPD4223	Phase 3
0.7262	Intermediate Similarity	NPD8264	Approved
0.7255	Intermediate Similarity	NPD6012	Approved
0.7255	Intermediate Similarity	NPD6014	Approved
0.7255	Intermediate Similarity	NPD6013	Approved
0.7245	Intermediate Similarity	NPD5223	Approved
0.7241	Intermediate Similarity	NPD4748	Discontinued
0.7241	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5701	Approved
0.7222	Intermediate Similarity	NPD1694	Approved
0.7216	Intermediate Similarity	NPD7638	Approved
0.7209	Intermediate Similarity	NPD3617	Approved
0.7184	Intermediate Similarity	NPD6883	Approved
0.7184	Intermediate Similarity	NPD7102	Approved
0.7184	Intermediate Similarity	NPD7290	Approved
0.7176	Intermediate Similarity	NPD6117	Approved
0.7174	Intermediate Similarity	NPD6672	Approved
0.7174	Intermediate Similarity	NPD5737	Approved
0.7172	Intermediate Similarity	NPD5211	Phase 2
0.7172	Intermediate Similarity	NPD4633	Approved
0.7172	Intermediate Similarity	NPD5226	Approved
0.7172	Intermediate Similarity	NPD5225	Approved
0.7172	Intermediate Similarity	NPD5224	Approved
0.7159	Intermediate Similarity	NPD4692	Approved
0.7159	Intermediate Similarity	NPD4139	Approved
0.7157	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD4519	Discontinued
0.7143	Intermediate Similarity	NPD5280	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD4694	Approved
0.7143	Intermediate Similarity	NPD4623	Approved
0.7143	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8035	Phase 2
0.7128	Intermediate Similarity	NPD8034	Phase 2
0.7115	Intermediate Similarity	NPD6869	Approved
0.7115	Intermediate Similarity	NPD6649	Approved
0.7115	Intermediate Similarity	NPD6847	Approved
0.7115	Intermediate Similarity	NPD8130	Phase 1
0.7115	Intermediate Similarity	NPD6650	Approved
0.7115	Intermediate Similarity	NPD6617	Approved
0.7111	Intermediate Similarity	NPD4197	Approved
0.71	Intermediate Similarity	NPD5175	Approved
0.71	Intermediate Similarity	NPD5174	Approved
0.7093	Intermediate Similarity	NPD6116	Phase 1
0.7087	Intermediate Similarity	NPD6372	Approved
0.7087	Intermediate Similarity	NPD6373	Approved
0.7083	Intermediate Similarity	NPD5210	Approved
0.7083	Intermediate Similarity	NPD4629	Approved
0.7073	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8297	Approved
0.7048	Intermediate Similarity	NPD6882	Approved
0.7045	Intermediate Similarity	NPD7525	Registered
0.7041	Intermediate Similarity	NPD5696	Approved
0.7033	Intermediate Similarity	NPD5329	Approved
0.703	Intermediate Similarity	NPD5141	Approved
0.7021	Intermediate Similarity	NPD5207	Approved
0.7011	Intermediate Similarity	NPD6114	Approved
0.7011	Intermediate Similarity	NPD6697	Approved
0.7011	Intermediate Similarity	NPD6115	Approved
0.7011	Intermediate Similarity	NPD6118	Approved
0.7011	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7614	Phase 1
0.6981	Remote Similarity	NPD4632	Approved
0.6957	Remote Similarity	NPD4690	Approved
0.6957	Remote Similarity	NPD4688	Approved
0.6957	Remote Similarity	NPD4689	Approved
0.6957	Remote Similarity	NPD4693	Phase 3
0.6957	Remote Similarity	NPD4138	Approved
0.6957	Remote Similarity	NPD6098	Approved
0.6957	Remote Similarity	NPD5205	Approved
0.6952	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5694	Approved
0.6944	Remote Similarity	NPD7115	Discovery
0.6931	Remote Similarity	NPD4754	Approved
0.6923	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4225	Approved
0.6852	Remote Similarity	NPD6868	Approved
0.6842	Remote Similarity	NPD5692	Phase 3
0.6827	Remote Similarity	NPD5168	Approved
0.6827	Remote Similarity	NPD4729	Approved
0.6827	Remote Similarity	NPD4730	Approved
0.6813	Remote Similarity	NPD4788	Approved
0.6813	Remote Similarity	NPD5362	Discontinued
0.6809	Remote Similarity	NPD5208	Approved
0.6809	Remote Similarity	NPD4518	Approved
0.6796	Remote Similarity	NPD4767	Approved
0.6796	Remote Similarity	NPD6008	Approved
0.6796	Remote Similarity	NPD4768	Approved
0.6789	Remote Similarity	NPD6009	Approved
0.6789	Remote Similarity	NPD6317	Approved
0.6778	Remote Similarity	NPD5369	Approved
0.6771	Remote Similarity	NPD6050	Approved
0.6762	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6926	Approved
0.6744	Remote Similarity	NPD4784	Approved
0.6744	Remote Similarity	NPD4785	Approved
0.6744	Remote Similarity	NPD6924	Approved
0.6744	Remote Similarity	NPD4687	Approved
0.6742	Remote Similarity	NPD4195	Approved
0.6737	Remote Similarity	NPD6904	Approved
0.6737	Remote Similarity	NPD6673	Approved
0.6737	Remote Similarity	NPD6080	Approved
0.6735	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6335	Approved
0.6727	Remote Similarity	NPD6313	Approved
0.6727	Remote Similarity	NPD6314	Approved
0.6707	Remote Similarity	NPD4224	Phase 2
0.6706	Remote Similarity	NPD7150	Approved
0.6706	Remote Similarity	NPD7152	Approved
0.6706	Remote Similarity	NPD7151	Approved
0.6703	Remote Similarity	NPD4269	Approved
0.6703	Remote Similarity	NPD4270	Approved
0.6702	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5133	Approved
0.6698	Remote Similarity	NPD5251	Approved
0.6698	Remote Similarity	NPD4634	Approved
0.6698	Remote Similarity	NPD5247	Approved
0.6698	Remote Similarity	NPD5250	Approved
0.6698	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5248	Approved
0.6698	Remote Similarity	NPD5135	Approved
0.6698	Remote Similarity	NPD5249	Phase 3
0.6698	Remote Similarity	NPD5169	Approved
0.6697	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD7732	Phase 3
0.6667	Remote Similarity	NPD1696	Phase 3
0.6667	Remote Similarity	NPD8039	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD4137	Phase 3

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