NPASS Compound

Structure

CID34190 OpenBabel06191715362D 24 26 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 0.8660 -1.5000 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 -0.8660 -0.5000 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 4.3301 -1.5000 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 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 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 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 -0.0000 -0.0000 0.0000 C 0 0 2 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 10 21 2 0 0 0 0 12 11 1 6 0 0 0 13 9 1 6 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 20 1 1 0 0 0 15 19 1 0 0 0 0 15 22 1 1 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	356.058
LogP:	2.318
LogD:	1.117
LogS:	-2.538
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.601
Synthetic Accessibility Score:	4.802
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.874
MDCK Permeability:	1.4166770597512368e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.107
20% Bioavailability (F20%):	0.091
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	61.94464874267578%
Volume Distribution (VD):	0.935
Pgp-substrate:	40.96001052856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.556
CYP2C9-inhibitor:	0.096
CYP2C9-substrate:	0.814
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.34
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	6.973
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.132
AMES Toxicity:	0.316
Rat Oral Acute Toxicity:	0.61
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.454
Carcinogencity:	0.078
Eye Corrosion:	0.399
Eye Irritation:	0.158
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC34190

Natural Product ID:	NPC34190
*Common Name:**	3Alpha,6Beta-Dihydroxy-7,17-Dioxo-Ent-Abieta-15(16)-Ene
IUPAC Name:	2-[(2R,4aR,4bS,7R,8aS,9S,10aR)-7,9-dihydroxy-4b,8,8-trimethyl-10-oxo-2,3,4,4a,5,6,7,8a,9,10a-decahydro-1H-phenanthren-2-yl]prop-2-enal
Synonyms:
Standard InCHIKey:	PYTXCJKULGAJQT-WEMZJFJNSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-11(10-21)12-5-6-14-13(9-12)16(23)17(24)18-19(2,3)15(22)7-8-20(14,18)4/h10,12-15,17-18,22,24H,1,5-9H2,2-4H3/t12-,13-,14-,15-,17-,18-,20+/m1/s1
SMILES:	C=C(C=O)[C@@H]1CC[C@@H]2[C@@H](C1)C(=O)[C@H]([C@@H]1C(C)(C)[C@@H](CC[C@@]21C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641878
PubChem CID:	53319172
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
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	8100.0	nM	PMID[565950]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[565950]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	7300.0	nM	PMID[565950]

☑ 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 NPC34190 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	217
0.1-0.2	1774
0.2-0.3	6482
0.3-0.4	14396
0.4-0.5	8438
0.5-0.6	5747
0.6-0.7	4245
0.7-0.8	1284
0.8-0.85	98
0.85-0.9	12
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9195	High Similarity	NPC272635
0.9195	High Similarity	NPC169751
0.8989	High Similarity	NPC219353
0.8989	High Similarity	NPC165616
0.8966	High Similarity	NPC99380
0.881	High Similarity	NPC146683
0.8721	High Similarity	NPC174619
0.8721	High Similarity	NPC153604
0.8696	High Similarity	NPC293890
0.869	High Similarity	NPC118800
0.8675	High Similarity	NPC328264
0.8667	High Similarity	NPC29112
0.8667	High Similarity	NPC142352
0.8652	High Similarity	NPC59350
0.8642	High Similarity	NPC476811
0.8602	High Similarity	NPC60947
0.8511	High Similarity	NPC272472
0.8506	High Similarity	NPC259009
0.8471	Intermediate Similarity	NPC471036
0.8471	Intermediate Similarity	NPC291320
0.8444	Intermediate Similarity	NPC59170
0.8444	Intermediate Similarity	NPC82138
0.8427	Intermediate Similarity	NPC80401
0.8427	Intermediate Similarity	NPC180849
0.8409	Intermediate Similarity	NPC472739
0.8409	Intermediate Similarity	NPC474925
0.8391	Intermediate Similarity	NPC269396
0.8391	Intermediate Similarity	NPC98236
0.8387	Intermediate Similarity	NPC288
0.8387	Intermediate Similarity	NPC109059
0.837	Intermediate Similarity	NPC135548
0.837	Intermediate Similarity	NPC5532
0.837	Intermediate Similarity	NPC192428
0.837	Intermediate Similarity	NPC61369
0.837	Intermediate Similarity	NPC264979
0.837	Intermediate Similarity	NPC469545
0.8352	Intermediate Similarity	NPC302008
0.8352	Intermediate Similarity	NPC191094
0.8333	Intermediate Similarity	NPC476168
0.8333	Intermediate Similarity	NPC185936
0.8333	Intermediate Similarity	NPC198242
0.8333	Intermediate Similarity	NPC168027
0.8333	Intermediate Similarity	NPC211403
0.8333	Intermediate Similarity	NPC278106
0.8295	Intermediate Similarity	NPC472495
0.8276	Intermediate Similarity	NPC190704
0.8276	Intermediate Similarity	NPC471034
0.8276	Intermediate Similarity	NPC76518
0.8261	Intermediate Similarity	NPC138245
0.8261	Intermediate Similarity	NPC84018
0.8261	Intermediate Similarity	NPC231060
0.8261	Intermediate Similarity	NPC41070
0.8261	Intermediate Similarity	NPC98639
0.8242	Intermediate Similarity	NPC294263
0.8242	Intermediate Similarity	NPC181594
0.8242	Intermediate Similarity	NPC144739
0.8222	Intermediate Similarity	NPC100313
0.8214	Intermediate Similarity	NPC476812
0.8202	Intermediate Similarity	NPC206060
0.8193	Intermediate Similarity	NPC106078
0.8193	Intermediate Similarity	NPC149249
0.8193	Intermediate Similarity	NPC472746
0.8172	Intermediate Similarity	NPC29410
0.8172	Intermediate Similarity	NPC200054
0.8161	Intermediate Similarity	NPC74595
0.8161	Intermediate Similarity	NPC474233
0.8161	Intermediate Similarity	NPC264665
0.8152	Intermediate Similarity	NPC104371
0.8152	Intermediate Similarity	NPC101233
0.8152	Intermediate Similarity	NPC289539
0.8152	Intermediate Similarity	NPC129004
0.8152	Intermediate Similarity	NPC153775
0.8152	Intermediate Similarity	NPC470385
0.8152	Intermediate Similarity	NPC91772
0.8152	Intermediate Similarity	NPC23170
0.8152	Intermediate Similarity	NPC111524
0.8152	Intermediate Similarity	NPC261333
0.8152	Intermediate Similarity	NPC293086
0.8152	Intermediate Similarity	NPC470386
0.8152	Intermediate Similarity	NPC292374
0.8152	Intermediate Similarity	NPC215271
0.8152	Intermediate Similarity	NPC29247
0.814	Intermediate Similarity	NPC48362
0.8132	Intermediate Similarity	NPC299185
0.8132	Intermediate Similarity	NPC250753
0.8118	Intermediate Similarity	NPC164999
0.8111	Intermediate Similarity	NPC472983
0.8105	Intermediate Similarity	NPC144956
0.8105	Intermediate Similarity	NPC55503
0.8105	Intermediate Similarity	NPC156324
0.8095	Intermediate Similarity	NPC476810
0.809	Intermediate Similarity	NPC472497
0.809	Intermediate Similarity	NPC165895
0.809	Intermediate Similarity	NPC57469
0.809	Intermediate Similarity	NPC4643
0.8085	Intermediate Similarity	NPC18509
0.8085	Intermediate Similarity	NPC10864
0.8068	Intermediate Similarity	NPC102292
0.8065	Intermediate Similarity	NPC139570
0.8065	Intermediate Similarity	NPC470232
0.8046	Intermediate Similarity	NPC243347
0.8046	Intermediate Similarity	NPC475726
0.8046	Intermediate Similarity	NPC175410
0.8046	Intermediate Similarity	NPC472743
0.8043	Intermediate Similarity	NPC472496
0.8022	Intermediate Similarity	NPC470378
0.8022	Intermediate Similarity	NPC149761
0.8022	Intermediate Similarity	NPC46758
0.8022	Intermediate Similarity	NPC183283
0.8022	Intermediate Similarity	NPC261994
0.8021	Intermediate Similarity	NPC148279
0.8	Intermediate Similarity	NPC89099
0.8	Intermediate Similarity	NPC38471
0.8	Intermediate Similarity	NPC162459
0.8	Intermediate Similarity	NPC158778
0.8	Intermediate Similarity	NPC26270
0.8	Intermediate Similarity	NPC230387
0.8	Intermediate Similarity	NPC471038
0.8	Intermediate Similarity	NPC28864
0.8	Intermediate Similarity	NPC20479
0.8	Intermediate Similarity	NPC38296
0.8	Intermediate Similarity	NPC328539
0.8	Intermediate Similarity	NPC98837
0.7979	Intermediate Similarity	NPC104568
0.7979	Intermediate Similarity	NPC329910
0.7979	Intermediate Similarity	NPC470387
0.7979	Intermediate Similarity	NPC13949
0.7979	Intermediate Similarity	NPC471039
0.7979	Intermediate Similarity	NPC140242
0.7978	Intermediate Similarity	NPC95594
0.7978	Intermediate Similarity	NPC158393
0.7978	Intermediate Similarity	NPC477579
0.7978	Intermediate Similarity	NPC235341
0.7976	Intermediate Similarity	NPC474433
0.7957	Intermediate Similarity	NPC280804
0.7957	Intermediate Similarity	NPC471207
0.7957	Intermediate Similarity	NPC475118
0.7957	Intermediate Similarity	NPC103527
0.7957	Intermediate Similarity	NPC471040
0.7955	Intermediate Similarity	NPC475745
0.7955	Intermediate Similarity	NPC470812
0.7955	Intermediate Similarity	NPC474482
0.7935	Intermediate Similarity	NPC474525
0.7935	Intermediate Similarity	NPC472978
0.7935	Intermediate Similarity	NPC198054
0.7931	Intermediate Similarity	NPC110780
0.7921	Intermediate Similarity	NPC100908
0.7917	Intermediate Similarity	NPC293866
0.7917	Intermediate Similarity	NPC15390
0.7917	Intermediate Similarity	NPC470388
0.7917	Intermediate Similarity	NPC291785
0.7917	Intermediate Similarity	NPC127408
0.7912	Intermediate Similarity	NPC184663
0.7912	Intermediate Similarity	NPC69627
0.7912	Intermediate Similarity	NPC472973
0.7901	Intermediate Similarity	NPC163020
0.7879	Intermediate Similarity	NPC265127
0.7872	Intermediate Similarity	NPC474602
0.7872	Intermediate Similarity	NPC470229
0.7865	Intermediate Similarity	NPC133954
0.7865	Intermediate Similarity	NPC292553
0.7857	Intermediate Similarity	NPC78935
0.7857	Intermediate Similarity	NPC96217
0.7857	Intermediate Similarity	NPC282233
0.7857	Intermediate Similarity	NPC95585
0.7849	Intermediate Similarity	NPC244356
0.7849	Intermediate Similarity	NPC12722
0.7849	Intermediate Similarity	NPC224060
0.7841	Intermediate Similarity	NPC472498
0.7841	Intermediate Similarity	NPC64600
0.7835	Intermediate Similarity	NPC252614
0.7835	Intermediate Similarity	NPC46848
0.7826	Intermediate Similarity	NPC126993
0.7826	Intermediate Similarity	NPC85173
0.7826	Intermediate Similarity	NPC46441
0.7826	Intermediate Similarity	NPC169933
0.7826	Intermediate Similarity	NPC191684
0.7816	Intermediate Similarity	NPC473217
0.7816	Intermediate Similarity	NPC164210
0.7812	Intermediate Similarity	NPC474793
0.7802	Intermediate Similarity	NPC143767
0.7802	Intermediate Similarity	NPC474677
0.7802	Intermediate Similarity	NPC472802
0.7802	Intermediate Similarity	NPC473229
0.7802	Intermediate Similarity	NPC474719
0.7802	Intermediate Similarity	NPC131470
0.78	Intermediate Similarity	NPC176949
0.78	Intermediate Similarity	NPC201908
0.7791	Intermediate Similarity	NPC470429
0.7789	Intermediate Similarity	NPC305483
0.7789	Intermediate Similarity	NPC62516
0.7789	Intermediate Similarity	NPC328162
0.7789	Intermediate Similarity	NPC223169
0.7789	Intermediate Similarity	NPC96859
0.7789	Intermediate Similarity	NPC157113
0.7789	Intermediate Similarity	NPC473158
0.7778	Intermediate Similarity	NPC213412
0.7778	Intermediate Similarity	NPC327115
0.7778	Intermediate Similarity	NPC2783
0.7778	Intermediate Similarity	NPC187545

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 NPC34190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	2294
0.2-0.3	3998
0.3-0.4	1823
0.4-0.5	424
0.5-0.6	175
0.6-0.7	121
0.7-0.8	94
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.837	Intermediate Similarity	NPD4697	Phase 3
0.8172	Intermediate Similarity	NPD5222	Approved
0.8172	Intermediate Similarity	NPD5221	Approved
0.8172	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD5285	Approved
0.8105	Intermediate Similarity	NPD5286	Approved
0.8105	Intermediate Similarity	NPD4696	Approved
0.8085	Intermediate Similarity	NPD5173	Approved
0.8085	Intermediate Similarity	NPD4755	Approved
0.8021	Intermediate Similarity	NPD5223	Approved
0.7938	Intermediate Similarity	NPD5225	Approved
0.7938	Intermediate Similarity	NPD5211	Phase 2
0.7938	Intermediate Similarity	NPD5224	Approved
0.7938	Intermediate Similarity	NPD4633	Approved
0.7938	Intermediate Similarity	NPD5226	Approved
0.7935	Intermediate Similarity	NPD6079	Approved
0.7917	Intermediate Similarity	NPD4700	Approved
0.7912	Intermediate Similarity	NPD5328	Approved
0.7857	Intermediate Similarity	NPD5175	Approved
0.7857	Intermediate Similarity	NPD5174	Approved
0.7778	Intermediate Similarity	NPD5141	Approved
0.7778	Intermediate Similarity	NPD3618	Phase 1
0.7742	Intermediate Similarity	NPD7515	Phase 2
0.7677	Intermediate Similarity	NPD4754	Approved
0.7667	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4788	Approved
0.7624	Intermediate Similarity	NPD5697	Approved
0.7549	Intermediate Similarity	NPD4729	Approved
0.7549	Intermediate Similarity	NPD6011	Approved
0.7549	Intermediate Similarity	NPD4730	Approved
0.7549	Intermediate Similarity	NPD6881	Approved
0.7549	Intermediate Similarity	NPD6899	Approved
0.7549	Intermediate Similarity	NPD5128	Approved
0.7529	Intermediate Similarity	NPD3703	Phase 2
0.7528	Intermediate Similarity	NPD3667	Approved
0.7525	Intermediate Similarity	NPD6402	Approved
0.7525	Intermediate Similarity	NPD4768	Approved
0.7525	Intermediate Similarity	NPD4767	Approved
0.7525	Intermediate Similarity	NPD6675	Approved
0.7525	Intermediate Similarity	NPD7128	Approved
0.7525	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD4695	Discontinued
0.7476	Intermediate Similarity	NPD6012	Approved
0.7476	Intermediate Similarity	NPD6014	Approved
0.7476	Intermediate Similarity	NPD6013	Approved
0.7474	Intermediate Similarity	NPD4202	Approved
0.7451	Intermediate Similarity	NPD5701	Approved
0.7404	Intermediate Similarity	NPD5135	Approved
0.7404	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD4634	Approved
0.7404	Intermediate Similarity	NPD7290	Approved
0.7404	Intermediate Similarity	NPD5249	Phase 3
0.7404	Intermediate Similarity	NPD5250	Approved
0.7404	Intermediate Similarity	NPD5247	Approved
0.7404	Intermediate Similarity	NPD5248	Approved
0.7404	Intermediate Similarity	NPD5169	Approved
0.7404	Intermediate Similarity	NPD6883	Approved
0.7404	Intermediate Similarity	NPD5251	Approved
0.7404	Intermediate Similarity	NPD7102	Approved
0.7396	Intermediate Similarity	NPD7748	Approved
0.7379	Intermediate Similarity	NPD7320	Approved
0.7379	Intermediate Similarity	NPD5168	Approved
0.7368	Intermediate Similarity	NPD8034	Phase 2
0.7368	Intermediate Similarity	NPD8035	Phase 2
0.7363	Intermediate Similarity	NPD3666	Approved
0.7363	Intermediate Similarity	NPD4786	Approved
0.7363	Intermediate Similarity	NPD3133	Approved
0.7363	Intermediate Similarity	NPD3665	Phase 1
0.7349	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7902	Approved
0.734	Intermediate Similarity	NPD4753	Phase 2
0.7333	Intermediate Similarity	NPD5127	Approved
0.7333	Intermediate Similarity	NPD6649	Approved
0.7333	Intermediate Similarity	NPD6869	Approved
0.7333	Intermediate Similarity	NPD5217	Approved
0.7333	Intermediate Similarity	NPD5215	Approved
0.7333	Intermediate Similarity	NPD6847	Approved
0.7333	Intermediate Similarity	NPD5216	Approved
0.7333	Intermediate Similarity	NPD8130	Phase 1
0.7333	Intermediate Similarity	NPD6617	Approved
0.7333	Intermediate Similarity	NPD6650	Approved
0.7308	Intermediate Similarity	NPD6373	Approved
0.7308	Intermediate Similarity	NPD6372	Approved
0.7264	Intermediate Similarity	NPD6882	Approved
0.7264	Intermediate Similarity	NPD8297	Approved
0.7204	Intermediate Similarity	NPD5279	Phase 3
0.7196	Intermediate Similarity	NPD4632	Approved
0.7176	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6116	Phase 1
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.713	Intermediate Similarity	NPD5167	Approved
0.7111	Intermediate Similarity	NPD7525	Registered
0.7079	Intermediate Similarity	NPD3617	Approved
0.7064	Intermediate Similarity	NPD6274	Approved
0.7059	Intermediate Similarity	NPD4789	Approved
0.7045	Intermediate Similarity	NPD6117	Approved
0.7041	Intermediate Similarity	NPD7900	Approved
0.7041	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD6317	Approved
0.6989	Remote Similarity	NPD4197	Approved
0.6989	Remote Similarity	NPD3668	Phase 3
0.6947	Remote Similarity	NPD3573	Approved
0.6941	Remote Similarity	NPD3698	Phase 2
0.6939	Remote Similarity	NPD6399	Phase 3
0.6937	Remote Similarity	NPD6314	Approved
0.6937	Remote Similarity	NPD6335	Approved
0.6937	Remote Similarity	NPD6313	Approved
0.6915	Remote Similarity	NPD5329	Approved
0.6909	Remote Similarity	NPD6868	Approved
0.6889	Remote Similarity	NPD6697	Approved
0.6889	Remote Similarity	NPD6118	Approved
0.6889	Remote Similarity	NPD6115	Approved
0.6889	Remote Similarity	NPD6114	Approved
0.6887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7100	Approved
0.6875	Remote Similarity	NPD7101	Approved
0.686	Remote Similarity	NPD4245	Approved
0.686	Remote Similarity	NPD4244	Approved
0.6842	Remote Similarity	NPD5690	Phase 2
0.6832	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD6083	Phase 2
0.6818	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6319	Approved
0.6814	Remote Similarity	NPD6054	Approved
0.6813	Remote Similarity	NPD7645	Phase 2
0.6804	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4221	Approved
0.6774	Remote Similarity	NPD4223	Phase 3
0.6765	Remote Similarity	NPD7638	Approved
0.6754	Remote Similarity	NPD6016	Approved
0.6754	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6015	Approved
0.6754	Remote Similarity	NPD5983	Phase 2
0.6703	Remote Similarity	NPD3671	Phase 1
0.6701	Remote Similarity	NPD5737	Approved
0.6701	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7639	Approved
0.6696	Remote Similarity	NPD6370	Approved
0.6696	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6059	Approved
0.6638	Remote Similarity	NPD8328	Phase 3
0.6638	Remote Similarity	NPD7604	Phase 2
0.6634	Remote Similarity	NPD5695	Phase 3
0.6628	Remote Similarity	NPD5360	Phase 3
0.6628	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6909	Approved
0.6609	Remote Similarity	NPD6908	Approved
0.6602	Remote Similarity	NPD5696	Approved
0.6581	Remote Similarity	NPD7492	Approved
0.6559	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7736	Approved
0.6542	Remote Similarity	NPD6008	Approved
0.6531	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6616	Approved
0.6525	Remote Similarity	NPD6336	Discontinued
0.65	Remote Similarity	NPD6411	Approved
0.6495	Remote Similarity	NPD4689	Approved
0.6495	Remote Similarity	NPD4693	Phase 3
0.6495	Remote Similarity	NPD7521	Approved
0.6495	Remote Similarity	NPD4138	Approved
0.6495	Remote Similarity	NPD4688	Approved
0.6495	Remote Similarity	NPD5330	Approved
0.6495	Remote Similarity	NPD4690	Approved
0.6495	Remote Similarity	NPD4519	Discontinued
0.6495	Remote Similarity	NPD7334	Approved
0.6495	Remote Similarity	NPD7146	Approved
0.6495	Remote Similarity	NPD5205	Approved
0.6495	Remote Similarity	NPD6409	Approved
0.6495	Remote Similarity	NPD6684	Approved
0.6495	Remote Similarity	NPD4623	Approved
0.6484	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7078	Approved
0.6408	Remote Similarity	NPD7614	Phase 1
0.6404	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4758	Discontinued
0.6395	Remote Similarity	NPD4224	Phase 2
0.6392	Remote Similarity	NPD1696	Phase 3
0.6387	Remote Similarity	NPD7507	Approved
0.6374	Remote Similarity	NPD7339	Approved
0.6374	Remote Similarity	NPD6942	Approved
0.6364	Remote Similarity	NPD6903	Approved
0.6337	Remote Similarity	NPD5281	Approved
0.6337	Remote Similarity	NPD5284	Approved
0.6333	Remote Similarity	NPD8293	Discontinued
0.633	Remote Similarity	NPD6412	Phase 2
0.63	Remote Similarity	NPD6101	Approved
0.63	Remote Similarity	NPD6080	Approved
0.63	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6673	Approved
0.63	Remote Similarity	NPD6904	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